i.e, you could be born in any province under any circumstances, and you could live however you wanted to live. You do have to take into consideration how you'd make your living, and also realism regarding the ES universe.
I'd probably be Witchhunter living in High Rock, I'm sure there are plenty witches to be a hunten' there ;) Either that or a travelling pilgrim.
So what about you?
I'd try to enter the politics, while at the same time, train my alchemy skills and try to learn a trick or two about illusion... If you got a brain, you already saw where I'm going...
Can you imagine? Littlefinger with mastery of Illusion and Alchemy? And if I could bring books from this world... The possibilities!
If my plans worked, I'd first have the entire Stone-Fist descendants hanged in public! And personally torture Rolff! OH MY LADY MEPHALA, I'M SO HAPPY!
And that'll never happen... Oh well.
An vampiric assassin-nightblade, in service to the Dark brotherhood or the highest bidder. Probably have a home somewhere in valenwood (even though i'd be a redguard). Live a parcially secluded life, venturing out for money and what not's. Ties to the thieves guide because all hail nocturnal. spend my days not assassinating making potions/poisons with the vast variety of plants in valenwood. One day marry a bosmer or dunmer once I decide to settle down.
Normally I wouldn't participate in a conversation like this; regardless, I'll bite.
I would be running a brothel in the Iliac Bay. It makes sense, considering every grown male needs some "physical interaction." When they're sick of not fulfilling their lusts, I'll gladly profit off of it and keep my business booming; it's a win-win situation for the both of us.