As far as other stuff..
Ruby: That sounds all perfectly fine, though I was going to say, the Arshea priestess seemed like it worked just fine and difficulty free, for example. I don't want you to frustrate yourself though, so, if you like your current idea, run with it. I would suggest something like maybe picking out an npc patron from ones getting listed up or something like that if you like though, and talking that out with me. That or I'll maybe give you double starting wealth or something if you're going to go all npc classes. Which I presume everyone else will be cool with. If you want your cohort to be all npc classes, that is also fine.
Kc: Stromford writeup looks cool as it stands now.
Phaia: Courtesan-ly type skills would probably be something like indeed profession, performance in things like dance or singing or both, knowledge local couldn't hurt, and appraise would help you run a business, unless you have bookkeeping minions to handle that for you (which you might), bluff, diplomacy and sense motive are all useful in social maneuverings besides.