Personality-wise, I'd be a Wood Elf, but in actuality I'd be Half Redguard, Half Breton, if it were to be my real self in Nirn. I'd probably wake up on a boat, since I'm not the kind of person to wake up in a cave or a prison alone. I'd make my way to Chorrol or Anvil, because Bruma would be ridiculously cold, looking at somebody wrong in Cheydinhal would get me killed, Bravil... just no, and Leyawiin has too much ethnic tension.
First things first, I'd learn magic from a trainer by becoming an apprentice to a Healer or a Mages Guild member who didn't go out much, no need to get myself killed. And being 16 and not the most athletic person around, I wouldn't be able to keep up with an Orc Warrior or a Khajiit Thief. I'd probably get a job eventually being something like an Alchemist, or a Healer, and I would make sure to always stay on everybody's good side.
Being technically a child, and seeing as how I'm a good person, I probably wouldn't have trouble finding someplace to live cheaply.
I'd make friends with people down by the inn, and hear stories of adventures, but I'd be far too afraid of dying to go dungeon-crawling. I'd train at acrobatics to the point that I could climb onto the tops of buildings, and then my alter-ego would come out. I'd learn to be a spy, simple as that. I'd dress in dark clothes, learn the secrets of the townspeople, and become a master of sneaking around. I wouldn't steal anything, because then I'd feel terrible, but I'd rummage through things to get information, as a hobby.
However, I wouldn't have anything holding me back from learning Archery, and eventually venturing out on my own. I'd always stay near a road, never carry much with me (Highwaymen), and I'd wander the safer parts of the wilderness. I'd eventually make my way towards Imperial City, and buy a home in the Waterfront District. Nobody would be able to tell I wasn't Middle-Class. I'd bathe often, wear decent clothes, and I'd visit bookstores often, so I'd be well-read.
I'd get a job as a cook in an inn, and work my way up until I was getting a nice enough income to move to a nicer part of town, and I'd invite my Beggar friends over to eat... although I'd keep a close eye on them.
Then I'd live happily ever after... until I made enough money to make travels to distant lands and meet new and interesting people while still being in a caravan so I'd have a very low chance of dying. Not to mention I'd study things like Lycanthropy and Vampirism, but I'd never actually get near a vampire aside from Count Hassildor, who I'd identify immediately 'cause I'd notice the teeth. I'd study in Alchemy and Healing enough to be able to cure Vampirism and Lycanthropy, and I'd do it for free to those who wanted the cure for themselves.
People who just wanted a cure handy, I'd make them pay.