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What you're saying is hardly unreasonable at all. Boiled to its essence, you're saying:

I want a character who doesn't require much suspension of disbelief be expended to explain why he runs with group X for an equal share of the treasure. (A very very few groups with level-shares or other 90s start-up like treasure division rules excepted).

So what you want is a character in the same general optimization envelope. If you're a more intrinsically powerful class, like wizard, optimize less than the party average, if less so, like a rogue or fighter, optimize more.

Bill them as guest star positions. A lot of older gamers with kids use those to scratch an itch every season or two. Frequently the guest stars are controlling major NPCs or BBEG major minions.

If you're the GM, I suggest the following:
First and foremost, show the existence and prevalence of the countermeasures BEFORE the pcs get access to the spells. Otherwise they're likely to feel that you're metagaming against them. You can have higher level npcs or governmental types discuss the matters with them in appropriate contexts (how are we going to keep Black Bart's minions from finding him now that we've finally imprisoned him, etc).

I suggest including a number of non or low magic defenses against teleport/divination/scrying in your game. The most recommended one is to have it blocked by sufficient earth and stone---like a magical fallout shelter, different materials have different amounts required for the effect. This also gives an organic, in-game explanation for why there are so many dungeons. You can also make certain areas (rich in certain magical ores), more effective in this regard.

I also suggest the one spell level metarule---which is to say that a prepared defense with access to spells one level or less than the offensive side can block the use of teleport/divination/scry. This is already implemented at the very high end (mind blank at level 8), but you should implement it in your game with weaker versions going down to much lower levels.

Ask yourself this, say you're a BBEG with fairly reliable access to contact other plane/commune/divination/etc. What are you going to do as Standard Operating Procedure? How can it be defended against? If the answers to those questions aren't to your liking from a balance or aesthetic point of view, I suggest creating new spells or house rules to generate the answers you prefer. And, per rule number one, do it and advertise it BEFORE anyone becomes too heavily invested in said capabilities.

Divination/Scrying is a lot like Electronic Intelligence (ELINT) in the real world. Think of a caster with access to level 9 spells in that regard as a lot like the NSA. ELINT has serious limitations. I'd suggest reading some of the fictional and real accounts/stories to give you a better handle on how to GM it. Rogues SHOULD be the masters of the other side of the intelligence coin (human intelligence-HUMINT). I suggest using house rules as necessary to ensure that they dominate that arena just as thoroughly as clerics and mages dominate the virtual ELINT one.

The social skills are broken, from an aesthetic point of view at minimum. Most GMs I know ignore them. None of the GMs that I know are willing to let significant success/failure (as in failing an adventure) hang on one of said die rolls. It usually only takes one optimized diplomancer to break a GM of all faith in that portion of the skill system. Sorry to be so blunt but it is what it is.

Whirlwind and Great Cleave (cleave is often worthwhile regardless) suffer from a synergy metagame problem. You see, they're balanced based on how powerful they are in a fully synergized build. To not be overpowered in a min-maxed build in other words.

What's a synergized build for whirlwind/great cleave?
Two handed reach weapon, habitual enlarge spell (or size large to begin with), lunge, and probably combat reflexes to boot.

What's a fully synergized build? All of the above, plus a party that focuses on doing AE damage as a matter of course (add optimized blasters, other street sweeper builds like yours, and maybe one archer damage hose build to pick off the stragglers after the AE smackdown is laid on.

To not be overpowered in the synergized or fully synergized cases, it makes it rather gimp for a lot of normal builds.

One high level mystic theurgist in my games (MT is the closest equivalent, she's a homebrew class that's I've had in many of my games since 2nd edition) has tons of simulacra of herself wandering the various planes of existence. They're her administrative and intelligence network. She's also got a really low bandwidth spell a la the sending spell to communicate with them periodically.

My normal ruling on simulacra is that while they'll follow your direct orders, they do have a will of their own when it isn't explicitly overridden and will gravitate towards doing what their original would do. Particularly strong willed originals with a legalistic bent will sometimes deliberately play with the letter/spirit of your orders so as to better accommodate their own desires and nature.

A few of these Elena-simulacrums, especially the ones that are at or beyond Elena's effective locus of control (some are totally incommunicado, others have an effective information bandwidth of like 200 or so words each way per year) are effectively independent agents with her approximate value system at the point of their creation.

You could just find a cleric with the law domain and use the domain power they get at first level which lets you 'take 11'.

Were I redoing all of the classes, I'd have this at the top of my mind:

It is REALLY hard to balance classes with burst/nova power against sustained DPR/utility power over the constellation of game types. The fighter, and to a lesser extent, the rogue, don't really have a lot of N times a day burst powers. This makes their balance point exceptionally sensitive to how the game is run. That in turn tends to make all sorts of metagame intrusion come into play (artificially forcing timetables and number of encounters/day for balance reasons rather than in-game reasons). So honestly, were I doing a rebuild, I'd arrange fighters and rogues to have significant 'burst-type' powers.

The central problem with the rogue is this:

Very few GMs are willing to let success/failure/whether and adventure happens at all ride on a skill check. And, of those that are, very few don't consider the skills that the party actually HAS in setting the DC. Thus if you're incredibly tricked out for high DCs as a rogue, well, those challenges will either be optional and/or set to not feel trivial given your skills. These metagame issues seriously hammer the rogue in anything but a hardcore simulationist game (where, for instance, the DC for gather information about plot X is Y, no matter what level you are or what your party composition is because its the DC that is set by plot X's spymaster's skills and the quality of his counterintelligence network).
A lot of Gms even formalize this into things like the 'Three Clue Rule'---where there are at least 3 avenues to get from point A to B in an adventure. This is grand from a gamist point of view, but in my view, if a rogue who is really skilled isn't getting you more adventuring opportunities AND better ones (i.e with a better risk-reward calculus), he's not really doing his job, or more likely, being allowed by the GM and the metagame to do his job.

Here's the deal, if you have multishot in an E8 game, due to prereqs, you're pretty well optimized. An optimized PC among a bunch of non-optimized pcs pretty much always appears strong. The tactic naturally taken by archers (damage hose single targets until dead, repeat with next target), is also one that Pathfinder favors since half-dead monsters still hit just as hard and as often.

The harshest setting-specific rules I've used for casters basically combined this:

Melee (and ONLY melee) full attacks took a standard action (thrown and ranged full attacks still took everything but your 5' step that round).
Spells by default took your full round, excepting the 5' step.
Concentration checks didn't exist, any damage or failed saving throw or grapple in effect automatically made your spells fail.
Melees were given enhanced ability to 'hold the line' through additional class abilities based on BAB (the main feature being the ability to designate an adjacent square as 'occupied by them', with an extra square if they have a shield, and extra squares at bab 6, 11, and 16 reflecting their ability to always 'be in the way' like an American football offensive line).

My observations with this is that groups of 6 STILL took an arcane and a divine caster, they just stacked the group with less of them than they usually did.
The balance

Is the crafter a gimp otherwise? In other words, is his ability to craft a significant fraction of what makes him 'worth his freight' as a party member collecting an even share of the treasure?

If the answer is no, and it usually is, ask yourself this:

If an NPC were to offer to make stuff for you at 60%....would you take it? I bet you would. In fact I bet you'd consider it a massive boon and you'd kiss up to him.

Generally in my games, adventurers often have a sideline of some sort besides their adventuring careers. They don't usually expect to get stuff from that sideline from other pcs totally gratis. If on the other hand your game is everything in the dungeon and nothing outside the dungeon, your POV makes sense.

Diplomacy/bluff/intimidate has so much table variation that it is insane, almost like enchantments, divinations, and illusions. Find out how your GM rolls insofar as your area is concerned. Then find out how much of skills X,Y, and Z you need to get the results in his game that you're after. If that amount is too rich for your blood consider the next tiers down.
Most of the time, at most tables, you can get by with nothing but a charisma of 12 or so, full ranks, and a minor emphasis on skill enhancing magic items. Another secret is this:
If you're not playing in my games, or games run by seriously hard core simulationists
VERY RARELY will you fail an adventure, or even a major objective solely because of a skill roll. Few GMs are willing to let an adventure hang on (or an adventure to not even start because of) what amounts to a single die roll. You'll find in practice that whatever you allocate, as long as it is a plausible investment (e.g., maxing that skill's ranks or even just having +5 or so more than the next best party member), it'll be enough. This is, in fact, one of the major problems of the rogue class. I'm willing for a group of characters to NOT learn of plot X because their intelligence network and gather information weren't up to the task. What happens then is that plot X proceeds without intervention by the PCs. Very few GMs are like this. Know your GM.

Also, remember that most people throughout most of their lives 'take 10' almost all the time. The next most common thing, pretty rarely honestly except when you're learning something new, is the repeated trials until you 'learn' or 'accomplish' something---ie an attempt takes x time, keep rolling till you meet the DC. So a +1 or +2 over your competition makes a HUGE difference.

I normally play it as a +2 or -2 representing a standard deviation from the mean. So somebody with a 12 in a stat is in the mid 80s in terms of percentiles for that attribute. Noticeably better than the norm---linguistically we start pulling out the adjectives here, like 'smart', 'strong', 'quick', etc. At 14, we start adding modifiers, like 'very' or 'really'. That's around the 98th percentile, so a lot, if not most, people's social circles will contain somebody at this level. Around 16, people pull out the lesser superlatives, like 'extremely'---you get somebody like this every few hundred. 18 is up at the one in several thousand level.

I'd suggest taking a serious look at how the save failure rate in climactic encounters changes as a function of how many rounds have passed. I wager that in 80% or more of games you play in, it has a steep upward curve as N increases. This is of course a polite way of saying the blunt truth: Most GMs are inclined to fudge heavily against a high DC SOS/SOD caster if he frequently tries to 'Indiana Jones' the BBEG. Know your GM. Frankly that's more important than knowing the rules of how to raise your DC. The 'God' caster archetype favored by Treantmonk is as much about avoiding GM and party aggro than it is about game mechanics.

The best counterspell in high level pathfinder is a high damage spell, preferably one that doesn't require SR. The best debuff is death. Perhaps you should just set up to burst him down before he can do anything? Maybe delay actions strategically so that he goes either before all of you or after all of you? After all you can't teleport if dead/unconscious.

Ask yourself what you'd do, as a PC, if you had vast resources and wanted to maintain a huge open-air prison for creatures/persons of moderate level.
What I'd do is some basic physical defenses, like walls and the like, but supreme magical intelligence. E.G, every week, perhaps more often: Commune spell, who/what/when/where will try to break out this week. If the opposition can't counter those divinations, you'll have total strategic superiority. Basically anyone trying an escape without mind blank or the like has set themselves up for a scry and die, which you should apply incredibly ruthlessly. Periodically, you ask about any developing powers in your prison (i.e., who is gaining levels, too many followers, etc). You deal with those accordingly. Supplement this with informants and non-magical intelligence. This'll work up to level 8 or so.

I'm a firm believer that pcs should be offered nearly any amount of rope they would like with which to hang themselves. Do your research (gather information, intelligence networks where rogues excel and fighters do well, magical intelligence via spell), and you can find lots of things that you can attempt or estimate the difficulty of the ideas you came up with. Then consult with your party whether they think the estimated reward is worth the estimated risk. I don't tune encounters to PCs normally, unless I'm running a miniseries where I'm going more narrativist/gamist than simulationist. That ogre lair exists whether you choose to go there or not, and it has some number of ogres with a mean of X and a standard deviation of Y no matter what level you might happen to be. What is incumbent on me as the GM is to make the information available within reasonable due diligence for the pcs to decide what they want to do, what jobs they want to accept, etc.
And just because an NPC asked you to do something does NOT mean you can handle it, or easily handle it. Yeah they're likely to consider your reputation in deciding who to ask, but those peasants paying onerous tribute to the dragon every year might have overestimated you or underestimated their oppressor.

If you look at the strength lift chart, the strongest humans on earth are in the 22-24 range. This maps pretty damned well to my interpretation of stats. 10 is the mean, and every 2 points equates to a standard deviation. This means that an 18 INT, for instance, is the equivalent of someone 4 standard deviations from the mean. That's not quite 1 in 10,000 level. 20 is 5 standard deviations, and 22 is 6. I recommend that you look at mental stat increasers as being a lot like chipware/wired skills/wired memory from Shadowrun in terms of how you run the fluff around them---it is way easier to maintain verisimilitude that way. Not to mention the fact that the headband of INT gives you skills rather than skill points, which tends to support my interpretation. It is much easier to credibly portray, say, an 18 INT guy with 10 in net enhancements (so he's a really smart guy with tons of magical 'cyberware', instant recall with a large online memory storage cache, and magical focus) than it is to portray an 'organic' 28 INT.

Oh, and in terms of daily routines...I'd say 95% of what everyone does every day is 'taking 10'---sometimes taking 5 when we're not paying much attention. That makes a relative +1 a big deal. When we're trying to learn something new, taking 20 becomes important (as does, rolling until you finally hit the DC if you CAN hit the DC). In those cases, that +1 is also a big deal at the thin part of the wedge.

Are 6 figure automobiles rare and precious? Yes, but people have them. Adventuring PCs are the 1%, so to speak, and many of them become the .1% and .01% and beyond as they advance. Frankly I found a verisimilitude issue way back in 1st edition and BECMI with magic shops NOT existing, so I had them in limited forms even back in the late 70s/early 80s in my games. They were more of a broker/commission kind of thing, and they were cartelized, but the notion that you could sell an item but never buy one never sat well with me (the 1st edition DMG had item sale values for every magic item). If you want no organized trade in magic with a monetary intermediate in your game, you need to make magic items a LOT rarer than RAW. You also need to ensure that there's a reason why none of your players can reasonably start such a trade on their own. The YA fiction answer of 'nobody thought of that' is just patently offensive to my sensibilities.

Gods in game worlds can be thought of a lot like feudal overlords on steroids. They provide tangible benefits, regular miracles, etc and ask for tangible devotions. It's a 'god' relationship rather than a 'God' one. How do you convert people? By offering them a better deal or a more attractive philosophy. Or you can inspire them with your mighty deeds and great renown. If you're a rock star, epic hero, etc, people are going to incline towards your overlord as well.

Vuron,
You could also do what I've sometimes done, allow a higher level version of make whole that requires only CL, or even something less than CL. But I've found that when you drop the metagame sunders, the residue is small enough that my players don't sweat too much about it---it happens every now and then but not just because the GM wants to destroy something.

Ilja, use the law domain power and you're taking 11. Not really taking 10, just forcing the die to come up 11.

Ilja,
On contact other plane, if your GM allows you to take 10, you do. If he doesn't, you use the priest of law ability to 'take 11'. It's easier to assume 'best practices'. Most deities have an intel network that will put yours to shame.

You should assume that any prominent figure with access to divination spells on a regular basis is using them daily/weekly/etc to determine if there are any active assassination plots against them. Thus if you're not warded against commune/contact other plane/etc, you can assume that your cover is blown more or less automatically. This is just the magical intel side of the house (analogous to signal intelligence and cryptanalysis in our own world). In terms of human intelligence, of course they're going to have a spymaster effectively using gather intelligence and running a spy network. This is, of course, if the NPC is competent, wants to live, and has lived up until now. If it is someone brand new to prominence, they might be more sloppy.

What would your PCs do if it was an NPC that betrayed them?
Probably kill/imprison/petrify/etc that NPC and make sure they never came back. The same is appropriate for a PC regardless of whether they were roleplaying or not. The PC stamp on the forehead is the most prevalent (and to my opinion, the most obnoxious) form of metagaming out there. People put up with stuff from PCs that they'd NEVER tolerate from an NPC that they were in an equal-shares of the swag partnership with. One of the things that really really aggravates me as a GM is when a player pitches a new PC to me and wants ME, the GM to effectively spend metagame suspension of disbelief resources to answer the question---why would the other PCs want to adventure with yours?
I'll grant you a little slack, allowing you, to, for instance, say your character of appropriate background is a cousin or the like of another character, or an old army buddy, or the like, but I will NOT press you onto the other PCs through plot manipulation just because you're a PC.

Did you accept their surrender? Or did you shout back 'No Quarter' instead? If the latter, no problem. Armies do the 'no quarter' thing whenever they're ill equipped to handle prisoners. That's neutral. But if you accepted the surrender its another matter.

My take is this: Are you sundering for metagame reasons or because it is reasonably the best option available for THAT particular NPC as he perceives it at this time? Most of the time when you do sunder, you could have killed or crippled the guy whose stuff you just attempted to sunder almost as easily. Pathfinder damage/SOS/SOD tends to be really fast. There are some exceptions (like the superarmored tank that for whatever reason you can't just SOD/SOS) where sunder is actually an optimal move. But you DO carry multiple holy symbols/spell component pouches don't you? All my players do, even if they're not spellcasters. All part of strategic deception.

I've run games before where the disabled/dying window goes all the way down to negative (your full hit points plus your constitution). These are normally the games where raise dead/resurrection is not possible like my 'Dawn of History' series. It works pretty well. I also did away with CdG and various other similar effects in that series (CdG was just an automatic crit). The idea was that these 'Antediluvian' humans lived before the breaking of the 'Law of Death' (think Thomas Covenant here), and would very strongly cling to life. From a metagame perspective, I also wanted to do away with raise dead and the like without breaking higher level playability.

The fighter aristocrat might be a major or a colonel of an elite formation. The warrior aristocrat is likely the same rank, but of a more ordinary formation. Basically the first aristocrat mostly commands low level fighters, the second, mostly low level warriors and commoners. Both have seen the elephant, probably multiple times.

Bit of Luck really shines OUTSIDE of combat, when you want to minimize the probability of a really bad roll. The one for law domain that makes you 'take 11' is similarly good in such situations. Make sure you have one on hand if you do contact other plane with a GM that won't let you take 10 :-)

Buy a few pearls of power, level 1. Ask your mage to keep up an unseen servant (Johnny-on-the-spot) for you to hand you more quivers and arrows as required.

As a GM, I'm willing to not track arrows and such as long as:
1. You don't do something like dump strength. If you're extremely suspect for encumbrance I WILL audit you
2. You shell out for the various items expected of your character level and archetype. That means handy haversacks, efficient quivers, etc. You also are keeping up on your monthly lifestyle payments.
3. If you have fletcher or other crafting proficiency that is relevant sufficient to take 10 to meet your DCs I'll cut you a bit more slack on #2.

If you're not in compliance, yeah, you've got to track every quiver and every arrow. Most of my players stay in compliance.

As a GM, I found the builds players were presenting me with aesthetically unsatisfying when I used point buy.

For instance, if you are using the 2 stat points = 1 standard deviation approximation that I use...

I know people in the real world with 18 Strength, and considerably more in the 14-16 range. How many of them have 7 or 8 intelligence (common dumpstat)?
Not a damned one. I also know people with similar levels of intelligence. How many of THEM have 7 or 8 strength? Not a damned one either. The real world actually doesn't produce a ton of dumpstat wonders with 18s and 7s. What it actually does is produce people with one or two exceptional abilities and the rest somewhat above average. NFL players, for instance, are smarter on average, even with the concussions, than the groups they are drawn from. So are college cheerleaders. We make movies about 'Rain Men' because they are so rare.

So my solution was to offer my players several templates to choose from. They're all decidedly lacking in 7s, 17s, and 18s, although they 'cost out' to fairly high point buys. My intensely competitive (among themselves, they've learned not to try to compete directly with their gm) players are a lot happier with that solution.

The biggest strength of the 'God Wizard' style is this.
Unlike a highly tuned blaster or a SOD/SOS specialist, the God Wizard will RARELY encounter much direct GM or other player aggro, to borrow a MMO term. The GM won't get annoyed by a constant stream of 'Indiana Jones' takedowns on the BBEG with SOD/SOS spells with extremely high DCs, or by everything being evaporated by spell perfected (fill in the blank blasting spell here). The melees will also feel heroic longer than the system normally supports.

Here's an exercise for players. Estimate what the success rate is for your SOD/SOS spells used on BBEGs, Major minions, and minor minions as a function of the number of rounds that have passed in climactic encounters. I wager in most cases you'll find an upward trend as the encounter goes on that can not be accounted for by the various debuffs, dispels, etc that you've done or by expiration of limited duration effects. I would wager also that the slope would be steepest for BBEGs and nearly flat for minor minions. Frankly, future editions of the game ought to work this way---making such spells useful only after targets are significantly weakened.

The social skills in D&D are pretty much broken. Frankly, even games with much better systems for such like Exalted are broken also from an aesthetic point of view (especially how it essentially encourages you never to let a social monster speak a la the 'shut up Hannibal' trope).
In reality, nearly all social interactions involve all three, diplomacy, bluff, and intimidate.
For instance, I'm a fairly strong guy significantly above six feet. There is an element of intimidation in EVERYTHING I do socially in real life, even when I'm trying to be unassuming. People might think they are rationally immune to this but they're not. Their gut, which is doing a large fraction of their processing is evaluating the implicit threat my existence poses.
But amusingly, I never seem to experience any negative blowback from this passive intimidation. Nor do I generally when I use slightly more open intimidation (walk purposefully and express your requests in an imperative rather than a questioning manner, and assume compliance in many cases a step beyond what has been explicitly agreed to---this is sometimes called 'assuming the sale'.
Now your characters almost certainly radiate a lot more passive threat than I do. Had they said something akin to:
Stand down. This is a matter of national security.
I'd probably have had the guards falling over themselves to comply, assuming they are known by reputation and friendly. The guard's gut is processing like this:

These guys are way way more than we can handle
They're offering me a plausible face-saving out
they're not our enemies and we have no specific orders concerning them

So they're inclined to let you pass as long as you don't rub their faces in it. Retroactively if you wind up doing something heroic, they'll revise their memories to how they helped you. People just tend to think that way.

You've got to be really careful with shield other. I suggest combining it with other defensive buffs, like resist energy of the types being tossed around. But when you use it properly it partially defeats one of the trump cards of pathfinder and similar games (focus fire). By spreading the damage around you make area heals/channels a lot more effective and take advantage of the fact that damage doesn't really impede a character much until he gains the unconscious or dead condition. Handle with care but do handle it.

Matt,
I've generally viewed the rules as a reasonable, if crude, approximation to the laws of physics (and magic and sociology) that prevails in that particular world.
People in the real world tailor their training, personal development, tactics, and strategies to their estimation of our world's similar laws, why should adventurers be different? A special forces operator, after all, is probably the equivalent of a low level adventurer.

For instance, if your game rules heavily weight initial attributes vs learned skills, expect a heavier effort by NPCs to identify and train those with the innate talent than otherwise. Or vice versa if those rules are reversed. Similarly, if combat maneuvers are more effective vs straight damage than the norm, expect to see more trip, grapple, and the like. People whose business is warfare do notice these kinds of things. They will know what's nearly impossible or highly ineffective and condition 'what they want to do' based on that knowledge.

One big meta narrative I've used a lot is this:
An empire or empires will rise. They will populate to their carrying capacity---Malthusian trap as it were. Through magic and bigtime infrastructure improvements, they'll extend their carrying capacity but they'll have a hard time keeping up with population growth. This in turn will lead to wars of expansion for lebensraum. Eventually some random event or war will lead to apocalypse as the rug of carrying capacity is pulled from under the empire (just the druids/nature priests/etc pulling plant growth for a year or two will do it, a mini ice age, etc). Then the four horsemen ride. Typical campaigns are set in the aftermath of this, delving in the ruins. But it is a cycle that naturally repeats itself.

I've generally made the approximation that magic plus medieval tech gets you the equivalent of very early industrial revolution lifestyles. Plant growth, in particular, gives a pretty substantial yield increase each year, allowing a higher population density and larger cities (the agricultural area around each city where it is practical to transport food is more productive). This also allows races like the elves to get by on less farmland since they're likely to have more access to plant growth and similar magics. They might farm proportionately only half the land that similarly situated humans do, hunt and gather on the remaining land, and let land fallow a lot more often---say a rotation like corn/soybeans or clover/nothing/nothing.
Plant growth would take up a lot of the slack, especially considering that they're not scraping the bottom of the barrel in terms of land quality for agriculture like the humans probably are (planting 2x as many acres often doesn't give 2x the return, because you probably were using the best suited 1x to begin with).

I've rarely had any problems with system mastery gulfs at the level of players <-> GM. I don't believe in or require deus ex. There is precisely one thing that will regularly and predictably get you killed in my games. That thing is going after things or going into areas that are out of your league, either by intention or lack of due diligence in doing your pre-adventure research. You see, if you're a level 6 party of highly anti-optimized characters, and all you think you can handle are garden variety orcs, well, you CAN target said orcs. As a GM I'll make challenges of all sorts available to your party, and if you've got initiative, you can often engineer your own, and most of the time, you get to choose what your party does. The exception is the 'red cell', where another faction actively targets you instead, but this usually happens only as blowback and usually only at higher levels. The only thing I use the CR system for really is determining treasure and experience. My encounters don't really give a damn what level or competence your pcs possess. The onus is on the players to identify and go after challenges that they can handle.

BFobar,
Can't do that without stuff beyond core. Core only is what a lot of gms, myself included, are used to. Spell specialization, etc are what allow you to really ramp up the power of blasts.

Low level pathfinder is rocket tag. So is very high level PF. Low level fighters, barbarians, and the like essentially have a "Save or Die", where the save is your armor class with two handed weapons for an awful lot of threats. So too do casters with sleep, color spray, etc. Maybe your GM is used to parties full of skill monkey rogues, sword and board fighters, healbot clerics, and blaster wizards?

Set, that was in the D1-3 series---I think D1-2. Asberdies if I recall was his name. Essentially, he lived down there in the Underdark. That was his lair. You could encounter him or not depending on where you went.

MDT,
I'm not fond at all of the downtime rules in Ultimate Campaign. I find the retrain rules way way too generous (I have long standing preexisting rules for such I've talked about here before) and rules for businesses and investments way too stingy.

Foxdie13,
Is a tavern a reasonable business in a big city? Almost certainly yes. Is it a particularly risky business? Not especially. Does the PC have some kind of economic moat to differentiate his business from the competition that isn't easily duplicated? You'll have to answer that question. In this case, that moat might be the PC's heroic reputation in that area if he's got one. You say he's a new player, so most likely the answer is no.
Since he has neither an economic moat nor a big risk premium, I'd say that 10,000 GP counts as 5% capital. That is, it produces a net profit after taxes, bribes, wages, depreciation, maintenance, etc of 5% of its total per year. That means the PC can expect average profits of 500 gp per year. Were he to have an economic moat, provided, say by his earned fame from adventuring, he'd have 10% capital instead, giving him a profit of 10%, or 1000 gp per year.
If he was in an especially risky business environment, he'd be in the 10% or even 15% class, but that gives you license to inflict more challenges on his business.
For a tavern, challenges might be the thieves or harlots guild trying to muscle or wile their way into his operation, law enforcement leaning on him, unruly customers, and 'blowback' on some of his customers for their adventuring activities. Adventurers frequent taverns like this, so people retaliating against them are likely to go there too. The ordinary amount of this sort of minor mayhem is factored into the regular cost of doing business, but it's an existential risk for a business if, for instance, an angry red dragon comes and razes it to the ground.
Sources used include 'The Intelligent Investor' by Benjamin Graham, considered the father of the school of 'value investing'.

Ask your GM to use the optional rule where you get one BUILD point per level rather than one attribute point per 4 levels (since raising a stat 18 or higher costs 4 points, this works out precisely the same for most optimized builds, but really helps unfocused builds like yours. For instance, at level 8, you'd have 8 more points to spend, so you could raise 4 of your 5 13s to 14. Or you could raise the 14 to a 17 by spending all 8 build points at that time.

44) A patrol from the nearest (mostly) civilized area. They may or may not be favorably disposed towards the PCs. They're probably mounted if the terrain favors such, and are probably level 1-2 with level 3-4 officers and a 5-6 commander. Size typically between a squad and a platoon.

45) A mercenary company, from platoon to battalion size, either on the move or on a job. They're likely neutral to the pcs unless some special condition applies.

In general, most GMs I know, and myself, basically ignore your familiar UNLESS you do one of several things:
Have the thing run around or attack in melee to provide flanking or the like or
Have the thing UMD or otherwise cast
or
Have the thing deliver your touch spells

If you do none of the above, 95%+ of your opponents will ignore the familiar and the GM won't inquire about him. We don't care whether he's wrapped around your wrist, perching in your backpack, fluttering in the breeze, whatever. I have had players go the 'fake familiar' route though---where they actually have a bonded item but they have small disposable pets for the opposition to ASSUME that they're a familiar.