DMPC Pirate Build need help [3.5][Gestalt]

[Perpetr8r]

Ok yes I know DMPC = the Anti-Christ and Hitler had a baby I do not want to get into a discussion about that in this thread.

Our campaign is gonna be a mix of Pirates of the Caribbean meets Assassin Creed 4. The PotC will explain the magical and mystical nature of d&d and to explain monsters and spells. The AC4 aspect is the missions and fighting other humans and sailing around exploring.

So I want to make a Pirate or at least a skilled sailor. He is gonna be a mix of Captain Jack and Edward Kenway so that he is a bit off and charismatic loving to have fun and get drunk but also very loyal to his friends.
But I am favoring the use of an odd weapon like the Harpoon, Trident, and Nets to fight as well as using a Sabre or Cutlass.

We allow Pathfinder Material (I like their srd more then the d20 srd one)

The books available are the Core books ( Player Handbooks 1&2, DMG 1&2, MM 1-5), Complete Books, Stormwrack, Sandstorm, Races of Books, Tome of Battle/Magic.

[Deophaun]

PotC? Make sure he finds a way to get a sea turtle for an animal companion.

[Perpetr8r]

I considered it. We are gonna have the Aquatic races from Stormwrack (My Fiance likes the Merfolk style of the Aquatic Elf or Avanti)

Well I was thinking Swashbuckler comboed with Ranger or Scout (Ranger for the pet)

But I am looking for a good build who can use those weapons effectively.

[Urpriest]

Since he's a DMPC, which capacity is he providing that the group lacks? Do you need him to have trapfinding? Do buffing? Emergency utility stuff?

[Red Fel]

Shiver me timbers, laddy! Have a look at this (http://www.enworld.org/forum/showthread.php?327699-Shiver-Me-Timbers-It-s-Black-Jack-Wellesley!)! Arr, t'is a start, aye?

Seriously, I don't loathe DMPCs, if you do them in such a way that the PCs remain center-stage. A synergistic build, designed to augment what the PCs do, rather than replace it, is an excellent way to make your DMPC useful, but not vital. The build above, in addition to being incredibly amusing, is very good at giving boosts to anything the characters do, while hindering enemies and remaining highly mobile.

And singing some rough, racy, jolly sea shanties.

... Matey.

[Perpetr8r]

Well he is more of the fill a role or help out a role guy. We have a person who is the diplothief style of play as well as someone who normally goes things like Warblade for sheer damage output. Our third guy is still new to me but he tends to Min/Max one specific thing such as Crit Fishing or two weapon fighting. We might get the rare 4th who plays random characters so he is our wild card.

I do like that build btw I will likely use that on one side.

BTW to be honest I might not be DMing every arc in this campaign as everyone is a DM at one point or another. So I might end up as a player as well. We might split it 1-5, 5-10, 10-15, 15-20 with DMs shifting about.

[Perpetr8r]

So I am gonna use the Black Jack build on one side because it will be good for the whole party. Now I need another side of my gestalt.

Can anyone come up with something?
Since this seems to be a Cha based build what else can work? I have access to Lost Tradition to make a spellcaster or anyone with a magical tie change their ability score (This is open to all the other players as well.)

Edit:
Maybe Gunslinger 5/Swashbuckler 3/ (But I am not sure from there)
This grants Dex & Cha to damage with guns and Int to damage with his Cutlass which can be finnessed, same with his Harpoon which is a Light Melee weapon (At least the Kuo-Toan ver.)