I want to make a character based on Cayden Cailen, someone who uses his great Cha to just rock the world around him. It is a Gestalt Game so he is gonna rock a few people with that alone.
I was thinking things like Swash//Warpriest (With Dynamic Priest for Cha casting)
Paladin//Swashbuckler
Swashbuckler//Bard
Bard//Paladin
Those are my general idea, of course my weapon of choice is the Rapier, with best way to enhance its threat range.
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Swashbuckler/Bard sounds like a very apt and effective choice - I'm not sure why you're going for Paladin, given the alignment incompatibility (although if you can cook up a decent CG Pathfinder Paladin in pursuit of this, that might work and more power to you - however, I'm unsure even CG Paladinhood would really fit Cayden Cailean's personal style).
How about a Summoner with a flying chandelier Eidolon?
Well I thought of maybe bring up the Paladin of Freedom Variant given that i am using the Gestalt rules from the same book.
Swash//Bard does seem to be pretty good, only real worry is Fort Save.
Better would be Daring Champion Cavalier/Bard. All the juiciness of a Swash plus three good saves and twice your level to damage.
Where are you getting "Dynamic Priest"? That's a 3rd party thing, right?
Swashbuckler/Bards are hilariously fun to play and it sounds a lot like Cayden Cailean. Like a barroom talespinner that can kick your ass with fancy swordplay. Warpriest would certainly work with Swashbuckler, and it would mean that your rapier would have a nice big damage die at high levels. Bard sounds much more thematic to me though.
Fort Save can be compensated for by using magic items or just having a high Constitution. After all, if you drink that much you must have a good Con score.
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Better would be Daring Champion Cavalier/Bard. All the juiciness of a Swash plus three good saves and twice your level to damage.
I did think of that, but in this case, I think true Swashbuckler would be superior. Cavaliers, mounted or not, are driven by commitment, and that's not really in Cayden Cailean's spirit (at least, not until they publish an Order of the Tankard or something).
Fort Save can be compensated for by using magic items or just having a high Constitution. After all, if you drink that much you must have a good Con score.
Or you did, until the cumulative liver damage hit home.
Dynamic Priest is from Dragonlance, it allows divine caster to change their casting stat to Cha from Wis.
I agree the Bard//Swashbuckler fits the theme
You could just be a Ronin (Knight Errant without the Eastern fluff) and make your own order with your own rules. Cayden Cailean is a very principled man, he just resolutely decides his own principles and doesn't let anyone else decide what is right for him. It's a fairly decent choice for an order regardless.
If I recall it was War of the Lance, Legend of the Twins
It is a feat, they also have Academic Priest which changes their Stat to Int.
https://dl-war-of-the-lance.obsidianportal.com/wikis/dragonlance-campaign-f eats
They have them here if you need to see them.
Needs some urban drunken brute barbarian. Add some duelist and chevalier prestige class levels maybe...