I admit, I like stealing things. (In-Game, of course.)
I have a classic assassin rogue, and I felt like joining the Thieves Guild was the way to go. I finished the Nightingales quest line and am close to being the leader of the Thieves Guild. But I am starting to get a little concerned about what I need to do to make it all the way.
I just refuse to go to jail. It's worse than losing the game; I'm not going to do it.