Building a Corsair.

[Dee_Twenty]

Greetings Playgroundians! Right, so, I'm currently involved in a high powered gestalt campaign and looking for some advice on how to plan out my character. He's a draconic (house rule in place, ECL adjustments for templates are halved and rounded down, so a 1 level template becomes 0) half-elf (aquatic, Races of Faerun version) fighter/daring outlaw (http://www.giantitp.com/forums/showthread.php?t=188150) gestalt currently at level 2, high stats due to template bonuses and rolling high. (Only two stats under 18, strength at 16 and wisdom at 12, with a 20 in charisma) and I'm having some trouble deciding what to do from levels 5-10.

I want to play him as a suave swashbuckling sort, a la Dread Pirate Roberts, focusing primarily on using his charisma, wits, and grace to solve situations, so, what I want to ask is, should I tale daringoutlaw and fighter until level 4, drop fighter and take two levels of half-elf paragon, 1 level of battle trickster, and 3 levels of uncanny trickster (raising battle trickster to 3), or take a one level dip in half-elf paragon, and five levels of fortune's friend then proceed as a daring outlaw/scarlet corsair? (both to their maximum pre-epic levels, 20 and 10.)

Please note that I'd like to keep things somewhat reasonable, I'm more interested in a character who will be both fun and exemplify the concept of a suave swashbuckler, not optimisation taking a bunch of classes that don't really relate to him as a character just to get a few class features. Suggestions for feats would also be welcome (currently have Improved Weapon Familiarity (so I can wield an elven thinblade and elven longblade) Weapon Focus (rapier), Quick Draw, Force of Personality, and Dragon Wings, (two flaws were taken for bonus feats.) I'm likely to take an exotic proficiency for either the gnome battle cloak or dueling cloak (Dragon issue 301) feat and Water Adaptation at some point.

Any and all official Wizards of the Coast books are in use, even different campaign settings such as Ebberon and Faerun since the campaign is using a custom world.

[Zaq]

Half-elf, you say? With Eberron material open? My friend, I may have good news for you. Normally, half-elves have very little to recommend them, but in this case, well, how would you like your very own airship? Crack open the Eberron Explorer's Handbook to page 70. There's a PrC there called Windwright Captain. The major class feature is AN AIRSHIP. (OK, it's kinda owned by House Lyrandar, but it's yours in a lot of the ways that really matter.) You get it at level 2 in the PrC, so it's not like you have to wait that long for it.

For the entry in the first place? I'd suggest Bard. To me, Bards make natural swashbucklers, and they make good ship captains as well, especially if you use some material from Stormwrack. (Every ship wants a Bard with the Windsinger feat. Is that worth one of your feat slots? Depends on the campaign, but it'll make you popular with the swabbies.)

If you want somewhere to go after Windwright Captain, you'll qualify for Dread Pirate pretty easily, but I'd probably just go back into Bard. Bards are awesome.

[Dee_Twenty]

Sort of, yes, it's kind of an amalgam of Eberron and Forgotten Realms, currently we're in Waterdeep, working for good old Elaith. Not quite positive if Lyrandar exists in this setting, might be able to convince the DM to let me adapt the class to work with an experimental new type of Halruan ship though, but then I could just skip the prestige class altogether and steal a regular Halruan airship, we're not a good aligned party anyway, as evidenced by my plan to become a Scarlet Corsair.

[hamishspence]

we're not a good aligned party anyway, as evidenced by my plan to become a Scarlet Corsair.

Which doesn't technically have an "any nongood" requirement, only "any nonlawful".

Still, a good scarlet corsair would be pretty unusual.

[Dee_Twenty]

True enough, though it's kind of hard to balance good with the whole spreading fear thing that a corsair is supposed to do, could probably prey exclusively on Zhent ships or something, I suppose that would probably count as good.

[hamishspence]

As long as the character avoids what the DM sees as morally unconscionable acts.

Quietly spreading stories to drum up fear of the character, rather than committing outright atrocities, would be the goal.