So I was thinking how to make a pirate character in 5e and I know the short answer is "swashbuckler rogue," but I wasn't completely satisfied with that. Swashbuckler definitely covers the suave, Eroll Flynn type pirate archetype, but it leaves out the violent, devil-may-care, grog-fueled  cutlass fighter pirate archetype. I initially thought it'd be fun to mix the swashbuckler with some flavor of fighter to get that mix down, but they mostly seemed too neat somehow.  I've never hugely drawn to barbarians as a class, but once it occurred to me that pirates as we've come to know them in pop culture essentially are dex based barbarians (don't wear armor, finesse weapons, hard to kill, skew chaotic), the more it made thematic sense that my ideal pirate character would be swashbuckler rogue/?barbarian. 

Now I know what you're going to say, "dex-based barbarians lose out on rage damage when not using strength weapons, bonuses to strength are also less ideal, mc-ing with rogue gives you less HP, etc." Sounds bad, but there are tradeoffs. For one, maxing out dex as soon as possible means probably higher unarmored AC than most barbs get early on, combined with Fancy Foootwork means you're really hard to actually hit. You maybe sacrifice a little damage for a little defense, and while it's still not by any means optimal, it's not nothing. That and, with finesse weapons, you always have the option to use either strength or dex with them, so as long as strength isn't a complete dump stat, you may still even have that option (though I'd still prioritize having good CON over STR). That and rage damage resistance plus eventually Uncanny Dodge if you make it that far can go far in negating what damage does come in. Not to mention, sneak attack once per turn (maybe even take sentinel for more opportunity attacks for additional sneak attack) goes a bit to offset lost outgoing damage. 

By that logic, the combo to me sounds definitely playable,  still not optimal, but optimal has never been my chief concern. My question, since along with never playing a barbarian before, I also rarely multiclass, so I was wondering what people thought the level distribution should be on this?  Would it make more sense to stick with barb till I get multiattack before focusing more on rogue, or take more rogue levels early on?

Im also not sold on a barbarian subclass yet. Berserker seems to be a good thematic choice, though I'm not sure how much I actually like it. Bear Totem's resistance-to-everything-but-psychic sounds real useful, as well as Wolf Totem's advantage granting ability, so I could see going with one of those. Storm Herald (sea) could be nice too, with the lightning aura effect taking the place of a flintlock or something, but really I'd only be tempted to go with that one if it was for a sea-based campaign. 

What do you think? Thoughts? Recommendations? Mostly doing this as a fun theory crafting exercise because im bored in quarantine so feel free to chime in! 

My problem with MC Barbarian is that it never feels like you have enough rages to be worth it. So many of the class features and benefits rely on that feature. After looking at what I can get with 5 levels of Fighter vs 5 levels of Barbarian, I drop the idea every time. It really sounds like it's just a matter of reskinning to me if you're really concerned about making a character that is somewhat optimized in combat.

Yeah I suppose I'd be relying more on high AC than damage resistance since rages would be more of a rare resource to spend with caution.