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Curious about any resources I should look into
You'll want to pick up Isles of the Shackles.
* Have GMs here generated interesting content I should look at?
There are LOTS of great threads with good improvements to the AP. A very popular one is on how to turn the AP into a more Sandbox-style adventure, which includes suggestions on other ways to treat Plunder. There are plenty more; I suggest searching through the Skull and Shackles Forums here for more ideas.
* What are issues with S&S systems? How could I address them?
This is more opinion-based, but Ship-to-Ship combat is pretty universally disliked. There are some good fixes out there, but I suggest checking out the system created by Dudemeister (can't find the thread to link it).
* Would it be feasible to replace the Plunder system with the Downtime Capital system? (i.e., turn Treasure and Plunder into free Labor/Goods/Magic/Influence capital the PCs could use)
Maybe don't replace it altogether, but make the Downtime capital rules able to be utilized with Plunder would probably work fine.
* Are there any interesting modules or adventures that could fit in with a pirate-y theme?
There are several, but the one I'm most familiar with is Plunder and Peril, which is for PC's levels 4-6, which means you could completely skip Book 2 of Skull and Shackles if you wanted to run this instead.
* What's the best way to make my game feel like a pirate movie?
That depends on what level of authenticity you're looking for. If you just want the loose, fun feel of a pirate movie, then I'd say just have fun with it and stay loose with the rules - let the PC's describe their heroic swashbuckling, and don't let the rules tie them down too much. If you instead want it to feel grittier, more real, then a good start would be to make it a low- (or non) magic settting. You could also look into sound effects, like ambient ocean sounds to add an extra layer of immersion.
Hope your game goes well, and everyone has fun! Good luck!
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worked for you in the past, I see no reason to not use it here. It doesn't kick in until level 3, so the PCs' lack of items at the beginning at least won't effect the narrative of having all their stuff taken away.
Background Skills is standard in any of my games. It's especially good in S&S because it lets players put ranks into Profession (Sailor) without worrying about losing ranks for more universally useful skills, especially for classes that only get 2 ranks per level.
I'd be careful of the Wounds rule. S&S is a very tough AP, and adding a scaling penalty to the players' rolls as they take damage could really snowball on them.
Adding guns is easy enough. Each Book gives you suggestions for where a gun or two can be added to an NPC or loot. I would warn any PC that plans on using firearms, though, that the first book deals with a lot of encounters that are either in Fog (Full Concealment beyond 5'), or underwater. Many players could get annoyed at being virtually useless so often. They'll have access to resources to mitigate these factors by Book 2's underwater combats, but Book 1 could leave them twiddling their thumbs a lot.
Story feats seem OK, but maybe consider having it cost 1 Trait, instead of getting it for free.
Curious about any resources I should look into or things I should consider. For example:
* What are issues with S&S systems? How could I address them?
Some parts of the plot will focus one one character, and may cause trouble with the other players.
Ship combat is another place where single PC getting most of the attention.
Choosing a captain can also cause an issue, if the group isn't willing to have one character be a captain. I have read of one group that made an NPC into the captain.
Skills are also important, not just perception, but also Profession(Sailor). It will be needed later in the AP, but high skill will be important.
Some things I'm looking at:
* Auto Bonus Progression.
* Background Skills
* Wound Levels.
* Guns setting that emulates black powder era.
* Free story feat (bonus points if players' story feats put them in conflict somewhere down the line)
Beware of adding in too many optional rule systems. You already have a ship combat system that most dislike. The more you customize things, the harder it becomes to keep track of everything.
Here is Dudemeister's variant. I don't knoe it, but someone mentioned not having the link, so I looked it up.
/cevah
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The ship combat system is a little wonky and I would learn it thoroughly and consider altering it to how you want it to work. The weather system is stuck in the back of the third book if you want to integrate it. I didn't see it until I was just starting that book and missed out on some harrowing possibilities.
Be aware that your group may attempt to use the alternate item creation rules from unchained to make boots to give them swim speed or something of that nature. I would consider banning it or getting really good at judging how much an item might cost based on what it can do.
I would also suggest (as Cevah mentioned) being wary of who the group choose to make captain and ultimately how much you choose to make that character the focus of attention (but for different reasons). I built my campaign around the character my players chose as captain. He then quit the game and I was stuck with his second mate... a character I could not find a single redeeming or even likable trait in. (I actually hated him).
There is a list somewhere on the boards of old adventures from Dungeon magazine a couple of which I had great success with.
Finally, consider making a change to dimension door where the portal is an open spot in space and not firmly glued to a surface so when they make it there is a chance that the moving enemy ship will leave it behind. Later in the campaign, before I ended it, my players ended every single ship combat with:
Everyone: "I delay until after the wizard."
Wizard: "I cast dimension door."
Everyone: *butcher enemy captain*
Morale condition: The crew surrenders upon the captain's death.
*sad Final Fantasy victory music*
The best supplement for sub-systems, character options, NPCs, plug-in adventures and ship to ship combat is the Pirate Campaign Compendium from Legendary Games.
I can second the Pirate Campaign Compendium; my wife got it for me for Christmas and it is AWESOME.
Almost all of the rules condensed from the 7 books (counting the players guide) into 1 book, plus a plethora of NPCs, 3 adventures, several encounters, new feats/archetypes, plus all the piratey lore you have to fish around for in the S&S books.
That being said, I am turning my currently running campaigns for S&S (I'm running 2, 1 in person and 1 on Roll20 for an NPO I'm a part of) into sandboxes after the visit to Rickety Squibs. So I have a ton of material.
Book 1 is an RP grind; if that suits your group, awesome. But YMMV.
Listen to the Called Shot Podcast for more excellent ideas; the episodes with the Iron Swarm are amazing for ideas for NPC enemies.
Background skills are handy; I suggest implementing them. S&S is skill-heavy. They'll need the extra points.
Ship to ship combat is a bit of a nightmare; I'm still trying to find a happy medium where it's easy to run, but satisfying for players in my Roll20 group.
Get fluid in your nautical and pirate lingo. It'll help with the immersion.
Player motivation is an issue; make sure they have characters that actively have goals in the Shackles.
My groups use Sandara and Ambrose as advisors. Sandara always advocates for high-risk, high reward plans while throwing caution to the wind. Ambrose plays things a bit safer and is more akin to a Mr. Gibbs for the party. I turned Sandara into an inquisitor as it made more sense to me than a cleric.
And note to self; look up the Living Grimoire archetype. That sounds hysterical.