
JKalts |

This may well be a "flavor of the month" deal, but I'm kicking around the idea of a character who features a style of combat based on Jeet Kune Do, which is effectively the antithesis to other martial arts due to it's prioritization of personalization and customization. And it's boiled down to whether to go Barbarian or Monk.
Since it's an unarmed combat style, Monk, and especially Martial Artist, "feels" thematically and mechanically like the best choice. Any abilities that don't seem immediately compatible could always get a fluff treatment.
By the same token, the style features methods of attack that rely on feinting and appearing weak, which screams "Come and Get Me" circa Barbarian. If Brawler and Improved Brawler weren't such traps as far as Rage Powers go, there wouldn't be a contest; just start off as an Urban Barbarian and go to town.
If I go down the Feint maneuver route, then maybe even Vivisectionist or Rogue might be worth considering, in order to make that flat-footed condition really hurt. Inquisitor with Broken Wing Gambit would fit the same vein without actually making them flat-footed, now that I think about it.
What I really need, is for someone to talk me into one set path. It doesn't need to be the cheesiest game-breaking thing you can think of, just something you can snapshot every few levels and get a gauge of how long it takes to get up to steam.
Oh, and this isn't PFS or 3rd-party friendly, just as a heads-up.

chaoseffect |

What level are you starting at? Also I'm assuming unarmed strikes are mandatory here, correct?
I would advise against going with the Feint route. It requires too many feats and even with Greater Feint it's iffy.
Master of Many Styles + Brawler Fighter is a nice combination. You could get early access to the Crane Style feats. Crane Riposte sounds like it would fit the idea you have in mind. Dragon Style does a lot for boosting damage or Snake Style line combos really well with Crane. Also note that if you go Master of Many Styles, you can skip the middle feat in a style chain using one of your MoMS bonus feats as long as you have the initial style feat (so you could skip the mostly useless Snake Sidewind and get Snake Fang using one of your bonus feats as long as you already have Snake Style).

JKalts |

What about Human with the Racial Heritage(Hobgoblin) and levels in Ironskin Monk.
Nab the Enlightened Warrior trait, then put levels in Barbarian.
This would negate the need for high wisdom.
You could even go Urban Barbarian, then be dex focused.
Ironskin Monk seems pretty potent; glad you mentioned it. I hadn't looked at any racial archetypes for the concept, will keep this one in mind if the GM mentions constructs.
Enlightened also seems like a good choice. GM has a bit of a prejudice against high-RP choices from ARG, but Racial traits shouldn't be a problem if I can work them into my backstory.
Would 8 Monk/12 Barb really be worth it? Worried I'd lose a lot of damage output, seeing how expensive an AoMF gets.
What level are you starting at? Also I'm assuming unarmed strikes are mandatory here, correct?
I would advise against going with the Feint route. It requires too many feats and even with Greater Feint it's iffy.
Master of Many Styles + Brawler Fighter is a nice combination. You could get early access to the Crane Style feats. Crane Riposte sounds like it would fit the idea you have in mind. Dragon Style does a lot for boosting damage or Snake Style line combos really well with Crane. Also note that if you go Master of Many Styles, you can skip the middle feat in a style chain using one of your MoMS bonus feats as long as you have the initial style feat (so you could skip the mostly useless Snake Sidewind and get Snake Fang using one of your bonus feats as long as you already have Snake Style).
We'll assume starting Lv 1 with a 20 PB for simplicity's sake.
Unarmed strikes are mandatory, unless you can point me in a direction that shows people using JKD with monk weapons or the like, in which case I'd reconsider.
Feint is a trap, I know, but I'd like to keep a few suboptimal options on the table in case I get a "character too strong, bring it in line or boulders fall" reaction from the GM.
Big thing for Brawler seems to be the inability to 5-ft away at Lv 9, but the bonuses to hit and damage would be the reason to stay longer. Maybe I don't see the synergy, since both are always 1 Lv away from getting their next new ability/damage die increase.
Style feats would take some flavoring, but I could see them working well in this build. I'll give a closer look to the ones you mentioned.