How did the quest croak? Also this happened to me once, I wasn't able to get a quest from the bartender because I had a ongoing Mabon's quest. Try finishing all quests before starting a new one with the Thief.
That's too bad about the crash, I personally have only had crashes when I alt-tabbed out while browsing the market. About the quest bug, could you describe it more in detail? The thief is supposed to give you a book? Or is it the quest where you have to retrieve the book for him?
I assume so, since arena fighters run at you really fast because of their athletics, and at the start a new game you don't see any tracks until you get scouting skill. Roguery, charm, steward and engineering however have no merit I believe.