I've read a lot of the other posts, some very creative others where a bit unrealistic, but I liked them ^.^
I'm a big LARPing fan, I love every minute of it, So if I lived in skyrim I think I would be:
An Adventurer. Traveling to see the world, to see all it has to offer poor little 'ol me. Searching hidden caverns with lush vegetation, hanging moss and trickling of water. The soothing breeze sweeping its way from the depths of darkness. Campfires, the smell of burning wood and a hearty meal. Enjoying the cool summer air with friends telling stories of old.
Traveling the land would have me encounter many trinkets of worth, dangerous obstacles. How can you pass on an exciting adventure like this. Maybe later I'll think about settling down, but not until I wet my whistle with adventure.
Make my own armor and weapons with the animal hides, feathers, fangs I carve off my kill. I would wear mostly Hide maybe with a bit of iron plate here and there from bandits who fall to my blade. I would carry two short swords, 5-6 daggers, quiver and bow, pack full of basic essentials(flint & steel, rope, toiletries, exe..), blanket, hatchet, and other useful adventuring tools.
A good adventurer needs knowledge about survival, geography, the lay of the land, and Lore. I would read often. You never know when you will need to be book savvy. Political concerns/views would not help me at all, but learning a bit of diplomacy will. Maybe to get me out of a tight situation and to establish my standpoint in society.
I love this subject, I'm glad it was posted...
Thanks