Armond Christoph gets rid of your bounty for you.. I do believe.
You'll eventually come arcoss a vampire or bandit wearing one, I don't even bother to pick them up anymore.
Ya fire away at the target and marksman should eventually go up, you might be a while, best to get people to train you.
Do the gulid line quests, Darkbrotherhood, Fighters gulid, theves, mages, and you will have no issues with money after that.