Boone by far is my favorite. His back story is pretty interesting and his sharpshooting skills do come in handy quite a lot. Not to mention is awesome beret!
I'd rather be born into the world as a vault dweller and eventually break away from it. I would hopefully have some basic resources to get me started. The transition would be a bit difficult but do-able. I'd prefer to find a small town to hunker down in with other waste landers