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So I want to make a Halfling Opportunist for Pathfinder Society (thus, RAW Paizo products only).
First, I have a question about what level I can first pick up the prestige class. Since two of the prerequisites are 5 skill ranks in particular skills, does that mean I have to wait until level 6 to become an Opportunist? Or can the character pick up the 5th skill rank in those skills at the same time as the 1st level of the prestige class, thus allowing the first level of the prestige class at level 5?
Second, I'm worried about not being effective with this class. The defining class ability, Exploitive Maneuver, is CMB based. If you follow the stereotype of starting Rogue before switching to Opportunist, then your CMB is hampered by the racial strength penalty, size penalty, and 3/4 BAB in both your base and prestige classes. You'd still be as good with sneak attacks as any other rogue, but the main benefit of the prestige class would probably fail more often than it succeeds.
So I was thinking that maybe Lore Warden fighter might be a useful base to build on. That way, you get higher HP, more feats early on, full BAB, and the +2 on your CMB at level 3, along with some nice int-based class skills that could be useful and the fluff to go with them. But the low skill ranks per level would hurt, and you wouldn't get as much out of your Opportunist sneak attacks without rogue levels.
So that led me to think of multi-classing Lore Warden with Rogue before Opportunist. Three levels of Lore Warden gets the +2 CMB and two bonus feats, while three levels of Rogue gets 2d6 sneak attack dice before the extra sneak attacks from Opportunist. This also mixes the best of both worlds for skills - almost everything is a class skill between the two, and there are plenty of skill ranks to go around.
Or am I just trying too hard to make the Exploitive Maneuver work, and I should just stick to Rogue/Opportunist like a normal person?

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So I want to make a Halfling Opportunist for Pathfinder Society (thus, RAW Paizo products only).
First, I have a question about what level I can first pick up the prestige class. Since two of the prerequisites are 5 skill ranks in particular skills, does that mean I have to wait until level 6 to become an Opportunist?
Yes.
Second, I'm worried about not being effective with this class. The defining class ability, Exploitive Maneuver, is CMB based. If you follow the stereotype of starting Rogue before switching to Opportunist, then your CMB is hampered by the racial strength penalty, size penalty, and 3/4 BAB in both your base and prestige classes. You'd still be as good with sneak attacks as any other rogue, but the main benefit of the prestige class would probably fail more often than it succeeds.
So I was thinking that maybe Lore Warden fighter might be a useful base to build on. That way, you get higher HP, more feats early on, full BAB, and the +2 on your CMB at level 3, along with some nice int-based class skills that could be useful and the fluff to go with them. But the low skill ranks per level would hurt, and you wouldn't get as much out of your Opportunist sneak attacks without rogue levels.
So that led me to think of multi-classing Lore Warden with Rogue before Opportunist. Three levels of Lore Warden gets the +2 CMB and two bonus feats, while three levels of Rogue gets 2d6 sneak attack dice before the extra sneak attacks from Opportunist. This also mixes the best of both worlds for skills - almost everything is a class skill between the two, and there are plenty of skill ranks to go around.
Or am I just trying too hard to make the Exploitive Maneuver work, and I should just stick to Rogue/Opportunist like a normal person?
I think any of those could work. If you'd really prefer to stay Rogue, consider picking up the feat Agile Maneuvers so you can use DEX instead of STR for your CMB. (Weapon Finesse will do that, too, for any maneuver that involves a finessable weapon.) Depending on your stats, that might be enough to undo all the penalties you're worried about.

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Yeah, the more I think about it, I think just doing a dex focused build with Agile Maneuvers will solve the CMB problem.
I've actually kinda been wanting to try a Dawnflower Dervish bard, but I wasn't sure if I wanted to go full bard with it, or just as a dip to get the Dervish Dance feat cheap and Battle Dance. So now I'm thinking I could start with a level of that so I can use dex for both attack and damage rolls right from level 1, then go Rogue and Opportunist the rest of the way for lots of sneak attack damage.

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So now that I've settled on my build progression (mostly), I do have some more specific questions about the Opportunist prestige class. Rather than quoting the whole thing, here's the link to the SRD entry for Halfling Opportunist.
First, I've searched and found other threads around here that say the Excellent Aid and Exploitive Maneuver abilities should stack. So even at level 1 Opportunist, your Exploitive Maneuver gives -3 to your enemy and +3 to yourself, even though the example says -2 and +2. Is there an official ruling somewhere I could print out and bring with me to show the random PFS GMs I'll be playing with?
Second, the description of Exploitive Maneuver sounds very cinematic, as if you're going to constantly be using it to do things like grabbing enemy's weapons to boost your acrobatics or something like that. And while that sounds really cool, it's not generically useful. The ability also says that it can be used to boost an attack roll or AC, besides just skill checks.
So does that mean that I can use it pretty much every time I'm attacked in melee? Only once per round, of course, since it's an immediate action, but I mean every round I'm attacked in melee, not just when the situation is specially set up to allow weird maneuvering. ie The bad guy swings at me, and I say "I'll try to watch and exploit the angle of his incoming swing, so I can to dodge it more effectively, and boost my AC." or "I'll try to watch and exploit the angle of his incoming swing, so I can dodge it in such a way that I land in a better position to hit him back, giving me a bonus on my next attack against him."
I'm just thinking that if I can use Exploitive Maneuver in every single round of combat, then it's a much better ability than I originally thought, even if it does fail half the time.
Next question, other than Agile Maneuvers, does anyone have any other recommendations for boosting my CMB so it works better. I also know about the Dusty Rose ioun stone that gives a +1 AC bonus, and happens to give +2 to both CMB and CMD when it's in a Wayfinder, so I'll be sure to pick that up. But if I'm going for Exploitive Maneuver a lot, I'd like to know about other options to boost CMB. Any thoughts?

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So I made this character and played him twice at a convention a couple of weeks ago. I also gave him GM credit for a session I ran, so he's up to level 2. He was pretty cool as a 1st level Dawnflower Dervish. I took Extra Performance as his first feat, since I'll never pick up more levels of bard, so the rounds of that aren't going to improve. This gives me 11 rounds per day with 12 charisma.
It was kinda funny to have the character introduce himself as a dervish swordsman, and then when I go to cast a spell at one point in the adventure, one of the other players was like "You're a spellcaster???"
I've advanced him to level 2 and given him a level in rogue. I find it amusing that he's a level 2 front line fighter with 0 BAB. Between the 19 dex, small size bonus, and masterwork scimitar, he's still got a +6 to hit, though, with an additional +2 while battle dancing, so he should be effective. And now he can get 1d6 sneak attack damage on top of his d4 +4 normal damage (again with an additional +2 while battle dancing).
I might be playing him this weekend in a PFS approved module, which would mean advancing to level 3 quickly, when he will pick up his second feat and first rogue trick. So the question is what feats and rogue tricks would be good for a Rogue/Halfling Opportunist with a one level dip in Dawnflower Dervish bard?
Defensive Combat Training is a prerequisite for Halfling Opportunist, and Agile Maneuvers will be necessary to be a successful Opportunist, so I'll need to pick up both of those by level 5. I might use Combat Trick to get one of them, so I can get an additional feat by spending a rogue talent.
I was thinking Improved Initiative, to up the odds of catching enemies flat footed for a sneak attack. Also, Combat Reflexes is probably too good to pass up for a dex based front line fighter. I was thinking of following that up with Bodyguard, especially since I have the Helpful halfling trait that makes my Aid Another actions worth +4 instead of the normal +2.
I don't really know rogue talents, though, since nobody in my group plays them very often. I was actually thinking Minor Magic might be good to get Acid Splash. That will give me something I can sneak attack with from 30 feet away during a surprise round while the enemies are flat footed, and it ignores both SR and DR.
What other rogue talents should I be looking at?

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Qassir, male halfling Sarenrae worshipper from Qadira
Favored class: Rogue
Str: 10 (2 point buy, -2 racial)
Dex: 19 (13 point buy, +2 racial)
Con: 14 (5 point buy)
Int: 10
Wis: 10
Cha: 12 (+2 racial)
I know, that's the lowest charisma ever for a bard, but he's not a real bard. I boosted the strength for carrying capacity (scimitar, chain shirt, misc equipment, halfling size penalty to carrying capacity, etc all add up). All future boosts will go on dex. All 3 of my classes will give 6 or 8 skill ranks per level, so I probably could have even dumped int lower if I really wanted. And with +2 Will from bard and +2 perception from halfling, I probably could have dumped my wis, too. If I wanted a dumb character, I could have gone int and wis of 8 to start with 20 dex, but I'm just not that much of a min/maxer.
1: Bard 1 (Dawnflower Dervish archetype), Dervish Dance feat for free, Battle Dance class ability 5 rounds per day (+2/+2 on my attacks)
Feat: Extra Performance, increases Battle Dance to 11 rounds per day
Spells: Expeditious Retreat, Grease (even if people don't fall, they're still flat-footed, and thus sneak attackable, if they move on the grease spot)
2: Rogue 1, Sneak Attack 1d6, Trapfinding
3: Rogue 2 - Need to decide on feat and first rogue talent
4: Rogue 3, Sneak Attack 2d6
5: Rogue 4 - 3rd feat, second rogue talent
6 - 10 Halfling Opportunist 1-5, with maybe one more Rogue level mixed in before level 10, if I want the extra sneak die sooner
As I said, I want Agile Maneuvers and Defensive Combat Training by level 5, probably taking Combat Trick at level 5 to get one of them. Improved Initiative is probably good for catching enemies flat-footed at the start of a fight for sneak attacks, so I'm thinking of taking that at level 3. And Combat Reflexes is just too good with this high a dex on a front line fighter, especially with that capstone Opportunist ability that makes all AoOs get sneak attack damage that I'll pick up at level 10 or 11.
I don't really know Rogue Talents, though, and I'll only get two of them before level 12, one of which will probably be Combat Trick to pick up those feats early. As I said, Minor Magic sounded good, so I can cast Acid Splash in the first round of a fight while the enemies are flat-footed, without having to draw a ranged weapon. But looking at the other options, Befuddling Strike looks pretty good, too.
Any suggestions on feats and rogue talents, and what order to get them?

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Was thinking about taking some levels in this too, and just wanted to run this by some people. Considering that the GM can allow another ability score than strength in CMB considering the situation, my finesse rogue shouldn't ever really have to worry much about his low strength, since he could just use dex to get a bonus to hit, or dex to get a dodge bonus to his armor class if he wanted to make sure he didn't get smacked.
Also, under the RAW, the opponent wouldn't necessarily even have to attack the halfling opportunist for exploitive maneuver to work, as long as the opportunist was within reach:
"the enemy must be able to reach the opportunist, and the opportunist must activate this ability as an immediate action and succeed at a combat maneuver check against the enemy’s CMD)"
So in theory, it seems to me that as long as the enemy was in range for a melee attack against the halfling, an opportunist could as an immediate action roll CMB if the enemy attacked someone else or otherwise performed an action the opportunist could think of a GM-approved way to exploit. Or does "reach" in this context mean any sort of action that could affect the opportunist, such as a ranged attack or spell (for example, the example given in the class description, where a halfling uses a fireball shot at him to help knock down a door)? Thoughts?

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The GM can allow another stat for CMB, but I wouldn't count on it without talking to your GM first. If you're in a campaign with a single GM, work it out with him in advance. If this is for Pathfinder Society, get Agile Maneuvers so you don't have to worry about it.
Personally, I haven't had a chance to play this PC since hitting level 3 over the summer. I think I ended up taking Improved Initiative as my level 3 feat with Minor Magic (Acid Splash) as my rogue talent, as described above. I'm still waiting to hit level 6 to get the prestige class.

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True. Luckily all the GMs I regularly play with seem to be pretty amenable to rule-compatible suggestions, so I wouldn't expect any huge problems even in my PFS games. I can definitely see the possibility for issues though. Personally, having gotten weapon finesse already, I'd rather take the chance that I just have to eat the bad CMD on the off chance of getting a picky GM, but if I wasn't already going finesse rogue I'd definitely take agile maneuvers.
The biggest potential problem I see is slowing things down by doing a complicated exploit every turn whether or not you are the one actually attacked or not (based on my above comment), but seems like that could be a fun problem to have.

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So I finally played this PC again a couple of times recently, and I'm just one adventure away from finally hitting level 6 and breaking into the prestige class. Now I'm trying to plan how to get a good CMB for Exploitive Maneuver.
Here's what I have so far:
1. High dex and Agile Maneuvers feat, so I can use my +6 dex bonus in my CMB instead of my +0 str.
2. Dusty Rose Ioun Stone in a Wayfinder, which adds +2 to CMB and CMD on top of the normal +1 AC.
3. Gauntlets of the Skilled Maneuver for +2 CMB to one specific maneuver. Just asked in the Pathfinder Society subforum for a PFS ruling on if these gauntlets will work with Exploitive Maneuver.
What else can I do to boost my CMB to help EM? It doesn't use a weapon, so weapon buffs don't help. I know anything that buffs my attack rolls otherwise will help, which includes my battle dance (Inspire Courage) from my one level dip in Dawnflower Dervish bard. But I don't have any other self buffs.
I don't suppose there's a feat or something that would let me use my level instead of BAB in my CMB, the way Defensive Combat Training does for CMD? Obviously, this is for PFS, so RAW only answers.
Any other CMB boosting items I may have missed? Or items that generally boost attacks without being tied to a weapon? Amulet of Mighty Fists only applies to natural attacks and unarmed strikes, but it doesn't mention unarmed combat maneuvers.