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Theme: Both S&S and WotR are based on established RPG adventure paths (available for purchase here on paizo.com), if you don't mind spoilers you can look at the product descriptions for the RPG adventures to see roughly what the storyline is for each one. That may help you make a decision on which storyline you like more, if that is your kind of thing.
Characters: No comments here, as this is purely personal preference. Do note that you can port characters from other sets and class decks into a particular game, so you could play S&S with a WotR character. However, each character from an AP is best suited for that AP, and the class deck characters are more generic "jack of all trades" types rather than specialized for the unique challenges of any individual AP.
Difficulty: WotR is still new, so I cannot comment on how the difficulty would ramp up or compare to S&S. I expect the checks to be higher due to the d20 and mythic path/charges mechanics, but also balanced out by those same mechanics. S&S does ramp up in difficulty far more than RotR does as you go onwards, decks 5 and 6 are very brutal.
Scenario Variety: See "Theme" above; the scenarios are straight out of the RPG storyline. When the story throws unique things at the players is when the scenarios get to break out of the norm. When it doesn't, then they don't. Since WotR doesn't have all the adventure decks out, I really cannot comment on how the variety compares to S&S but I'm pretty sure you'll see a nice mix of scenario abilities/effects.
Both APs should be fun and awesome (I had a blast playing S&S, and although I haven't gotten far into WotR yet it's been fun for the couple scenarios I've played). My recommendation is get both ;) or failing that consider also the release schedule.
S&S is fully released, you can get it now and play nonstop and finish it in short order. WotR is still being released, with each new adventure deck (5 scenarios each) coming out once a month. This means you won't be getting your hands on AD6 and the final scenarios of the story until 5 months from now. If your group doesn't play that often, that may be fine, but if they play a lot then S&S may be a better investment right now.
Also consider if you want the promo cards. If you do, your best bet is picking up a Card Game subscription here on paizo.com as you'll get every promo shipped to you as part of the sub. However, the sub is currently WotR-only, so if you go that route you'll be locked into WotR. You can still get S&S promos secondhand (with exception of Ranzak which is sold online here), but you can no longer get them through retailers or online here.
***Difficulty***
From what I read about WotR, it's pretty hard, but the opinions seem to be divided on whether it's unfairly hard, or just needs more careful management of information and resources than previous PACG adventure paths. Has anyone played through enough of WotR to give a more nuanced opinion on this yet?
I think that some of the assessments about Wrath's difficulty are overblown. What I will say is that the five scenarios in the base game are, as a whole, far more difficult than anything we have seen before. Their are several scenarios that make cornering the villain more difficult or have an incredibly high bane to boon ratio. Some scenarios force you to run a gauntlet of barriers, which makes it more likely to get the potentially show stopping draw of Arboreal blight or demonic hoard.
For me, it took me fourteen games to get two parties through the first five scenarios. Aside from a loss in Brigadoom in my first game, I haven't lost a starter game in wither RotR or S&S.
So why would I question the assumption that Wrath is far more difficult? Because once you hit AP1 things get much easier. You have scenario rules that make it easier to close locations. The boon/bane ratio improves in general, but more importantly you always have a small number of barriers. The new banes don't include anything nearly as tough as Arboreal blight,demonic hoard or corrupted golem, so adding cards actually dilutes the threat of bane overall.
I'm 8-0 in games in AP1. It doesn't seem harder than S&S, if anything it feel easier (though my mind could be playing tricks on me on that front. S&S difficulty ramps up nicely in later scenarios)
If you had to pick only one, I'd go for S&S. You really can't go wrong with pirates and high seas adventure, and the difficulty does ramp up pretty nicely.
Wrath's difficulty comes mainly from the VERY flavour-appropriate source of sheer randomness. The Worldwound is a crack in reality which is allowing the VERY ESSENCE OF CHAOTIC!!! EVIL to pour into our world, and untamed randomness is always going to be your worst enemy.
That, and the most annoying mechanics (things that do damage before and after you act, unavoidable deck pokes, etc) are hitting you right from the start.
It is perhaps worth note that there are plenty of Wrath dangers yet to come, in ADs with numbers higher than 1.
Wrath's difficulties do tend to be more slavering clawing mashing in your face damage rawr kinda threats, while Shackles tends to be ships crashing, you're drowning, someone sang away one of your party members kinda threats.
Honestly, they're both pretty cool. I'd say Wrath is slightly more complex and I like the characters in Wrath a little better, so I prefer it. At least half of that is because I got to work on it, and not Skulls and Shackles. So grain of salt.
End of the day, S&S has a very compelling theme, so in a pro-pirates and guns group I'd give it the nod, otherwise I'd stick to the more traditional theme and go wreck some demons.
I am not a fan of incredibly difficult games, so I'm coming at this from a much different angle, so here's my 2 cp. At this point I feel Wrath has been harder (only played the base set, though). However, it feels more 'fair' so to speak. S&S, especially certain later scenarios, can be very RNG dependent (The Bell Tolls, Bizarre Love Triangle, and Admiral Thune immediately spring to mind), and the game itself, especially with large groups, is already heavily RNG dependent (You have less time per location, so Henchman/Villains near the bottom are especially painful in 5-6 player groups). We failed 4 times on the base set, though at least a few of those can be directly attributed to poor play (exploring a location with someone that had no hope of closing it being the big one), and the rest are highly bad luck (not getting a 5 on 2d6 twice in a row, the aforementioned 'all henchman on the bottom' situation).
I believe the end result is that they're about equal in difficulty, though I hope Wrath will continue to feel less like it's less up to the whims of fate.
My 2 cents, wrath is super duper hard as solo with Balazar. I've been stuck on scenario three in the base set for awhile now. It took me 3 character deaths on scenario #2.. so yeah. I'm kind of shocked that its so hard. My hope is that after I get through the base set and get to deck 1 it gets better. Also, is it me, or are the spells harder to recharge than in earlier sets?
My solo strategy is to play 2 or 3 characters instead of just 1, helps even out the checks by picking characters that complement each other and allows me to get past otherwise nearly impossible things. That said, if you are soloing with 1 character and you do come across something that is literally impossible for the character to do, remember the rule that allows you to replace that thing with something doable but (roughly) equally challenging. For reference, I've reproduced it below:
Some cards are particularly difficult in solo play. If you're playing Enora by herself, and you pick up a Telekinesis Trap, you may be making impossible Acrobatics checks until you die. When you encounter a card your character just can't deal with, remove it from the game and replace it with another card of the same type that roughly matches its power level but isn't quite so impossible to overcome.
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If you've got a lot of time to commit, I'd say S&S purely because it's all out now and you can burn through it. When you're playing the game deck to deck, five scenarios don't spread well across an entire month, and Wrath will always be there waiting for you when you're done. If you really get into it, you've also got the option of paying a little more and getting all the Seasons of Shackles scenarios, which is a pretty good way to extend the life of what you already own and try more characters without running them through the same scenarios over and over again.
My wife and I share the opinion of "ick, yucky" when it comes to Wrath. When you go through a sequence of encounters like Worm Demon, Worm Demon, Giant Maggot Swarm, Giant Fly you start to feel a little put off. Like come on, there has to be a few greater demons that aren't centrally based in slime and vermin. At this point we'd even endure an overly sexualized succubus or two just to get a little variety! :D
(Giant Amoeba is super cute though)
(but that Giant Fly needs to stop screwing up Adowyn's carefully managed scouting >:|)
The determination of S&S as "fun" was the biggest pull for us. Even though it's been repeatedly said that Rise of the Runelords isn't meant to just be "generic fantasy scenario," that's what naturally springs to mind when you're wading through goblin hordes. There was a lot more interest for us in opening a new set of S&S to "wow, eel people!" because it was something we hadn't experienced in an RPG setting before--we've played a lot of Diablo, we know from demons. S&S is rich with flavor. Characters like Jirelle (half-elf swashbuckling pirate queen!) ring with a little more novelty than the stock archetypes of RotR so, at points, it really felt like playing a brand new game. I mean, the first Loot card you get in RotR is some mythical enchanted medallion (whatever!) and the first one you get in S&S is a magical tricornered hat (hell yes!)
S&S's Plunder smoothed out a lot of issues I had with loot distribution in Runelords. It's still random, but some scenarios give you so much plunder that you're bound to see something interesting. Or, at least, you get the pleasure of flipping over a pile of mystery cards at the end of a scenario. Maybe it's the lapsed Magic player in me, but the thought of sifting through 14+ unknown treasure cards kept me interested until the end of every single scenario. Where, judging all-too prematurely, I look at Mythic Paths and think, "that looks like another fiddly bit to keep track of in our very small NYC apartment with its laughably tiny dinner table" My guess is that Wrath is going to have a lot of things you really don't want to fail (if someone dies in the Family Tomb, everybody dies?) and that's what the d20 is about. That can be neat! But it remains to be seen if it's as rad as throwing every Blessing of Abadar you have at a Goblin Keelhaulin' and coming out the other side eight cards richer.
Don't get me wrong, it's not like we didn't play through Runelords 3-4 times, but coming to S&S was this cavalcade of fun-to-say names, places, and things--"Goose in the Rigging," "Tot Flask, ""Geffer Tibbs," and the #1 All Star "Barefoot Samms Toppins(!)"--where, sometimes, you'd hit a new RotR of like "so these grotesquely obese ogres are really hitting that weird X-Files theme episode, huh...?" And just have to grin and bear it.
Though, as a fan of creepy cults and the undead, I don't think I've liked the theme of any AP as much as I did The Skinsaw Murders. That really concreted our love of the game. I would play a whole PACG set about Scarecrow Ghouls and similar; I really hope there's some kind of Gothic Horror Pathfinder AP waiting in the wings for them to explore.
A lot of the game and it's difficulty is working around RNG, and that includes the shuffling of the decks and the rolls of the dice. The scenarios mentioned by isaic16 have a heavier shuffling RNG, but WotR will probably have an higher roll RNG overall. I'm actually more comfortable with the first kind than with the second as a tool to increase difficulty (and I'm pretty sure WotR will use its fair share of it too). Dice...
I've said it a lot of times on the forums, so I hope I'm not being boring by repeating myself, but we play with an extra location or two in our games; partially to increase difficulty, but also just to make the game last longer (5 scenarios stretched over 4 weeks, after all). S&S did a lot to make the challenge more interesting than RotR--causing us to ease back on our increase-difficulty-through-brute-force method--by forcing your characters out of rote specialization. Like, in RotR you'd never use a skill feat on anything but your primary combat skill until that was maxed. If something in Runelords was going to give you trouble before combat, it was almost always solved by a Ring of Protection or a buried Armor. S&S's diversified barriers, especially, made you go "wellll... maybe I should put that second skill feat into Wisdom, because I need to murder some ships and ~maybe~ crash into rocky shoals a little less often. I love the Temptation barriers in Wrath (especially since they go away without a fuss!) but there's a high % of "directly murder this group of monsters" with a distinctly un-Runelords rider of "and you'll be REALLY sorry if you don't."
As people have said, the difficulty in AP1 of Wrath slacks off a lot after the murderous first few scenarios of the B set. B scenarios are always weird in Pathfinder, their difficulty nudged a little harder than that's written on the cards because you're forced to deal with RNG a lot more--no skill feats or good blessings to buffer bad rolls--before your decks have gotten a few upgrades to smooth out rough patches (and, if you're using the Suggested Decks in the manual, maybe you're doing it with some really non-optimal Basic cards (like Potion of Anything)). Combine that with some notably mean-spirited banes (Arboreal Blight and Carrion Golem) right out of the gate and Wrath wouldn't be my first choice to introduce someone to the game. Between RotR being very straightforward, sometimes to the point of error, and Wrath's initial outlay being pretty grueling, S&S strikes the right balance of difficulty, interest, and fun. And, as the sophomore set, it provided what was missing in RotR: diversity. I loved item-based Merisiel to death, but she had more than one Magical Spyglass in her deck just because there was nothing as versatile to fill the slot. S&S gave us a lot of things that operated outside of the category norms Runelords had trained us to expect--Guns that add to your Wisdom check! Spears that aid your Constitution! Bandanas of Swashbuckling! Potions of Flying!--and that was just so fresh. It perfectly hit that feeling of "gosh, what will they think of next?" RotR character advancement decisions often boiled down to "okay, what gets me more dice on my combat check?" S&S was about "I think we need to keep this Ring of Fortitude, and Jirelle should put her first point in Constitution, just so the Sea Caves stop murdering us."
(also, thematically, you're encouraged to say "Yo ho!" a lot!)
However, following comments on the difficulty (and looking at the amount of adorable animal allies in SnS), made me switch back to SnS.
If you're looking for cute animals, S&S definitely has it in spades. I mean, look at this AP6 heavy hitter! In my estimation, she should make the choice for you.
+1 to everything Dave said. That was one of the best postings I've read on the Paizo board.
Yo ho!
Aw, thanks!
Though, looking at it now that it's posted and formatted, I apologize profusely for the wall of text. m(__)m
Haha, yeah. I don't want to take away from the sentiment that I am distinctly enjoying Wrath, it just hasn't clicked in the same way yet. As it is, we've stopped being "boardgamers" and now essentially only play Pathfinder while several sets of Descent, Lord of the Rings, and Netrunner linger on our shelves (I haven't even bought Manor of Ravens when, as mentioned, Gothic Horror is my #1 thing). At the rate we're going we'll play, and love, PACG until either Paizo dies or we do (from wasting away into nothing due to a lack of new Pathfinder).
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Though, as a fan of creepy cults and the undead, I don't think I've liked the theme of any AP as much as I did The Skinsaw Murders. That really concreted our love of the game. I would play a whole PACG set about Scarecrow Ghouls and similar; I really hope there's some kind of Gothic Horror Pathfinder AP waiting in the wings for them to explore.
It's called Carrion Crown.
He is talking about the card game, though.
There's some story guides for Rise of the Runelords and Skull & Shackles I worked on with BGG user Kittenhoarder that might sway your opinion. I created supplementary guides for the Blessings Deck and the Hero Origin stories that will assist you in picking up the Pathfinder lore within the context of the card games (I assume of course you have general D&D Monster Manual knowledge, because I didn't do a guide for the creatures.)
You can find these projects registered under the Community Use section of Paizo's website. It contains the necessary links to Boardgame Geek so you can download the files.
Theme: Sounds like you know what you like.
Characters: Sounds like you know what you like.
The cohorts are ally cards that provide a boost to help you overcome the significant challenges in Wrath. They're still cards that are in your hand.
Difficulty: Wrath isn't just an increase in numerical difficulty, it's a different way of thinking.
There are more interesting effects on the creatures and locations. The challenges have increased but you'll also have lots of tools that will help you meet these challenges (mythic paths, cohorts, loot).
When I was playing, the only times we came close to failing was when someone made a strategic mistake in either deck building or play. At least the possibility of failing is there. Haven't failed yet however in AD 1/2. I believe it will get more difficult in AD 3+ unless Paizo gets unnerved by the difficulty feedback in the B set.
Scenario Variety: I think the scenario variety is good in both products. They're just different flavors.