I think i've about done everything you can do in the game quest-wise. My dude basically runs shit in all possible ways, though somehow all of the guards in the game hate his guts(perhaps it was the dark brotherhood questline). It took a mere 110 hours. One nice little trick that i didn't try until pretty late in the game is to enchant 5 different pieces of clothing with 20% chameleon. It's like being invisible, except you can attack people and open doors and steal as much as you want without anyone even really knowing you're there. Enemies can't see you and don't attack. You can still manage to wrack up a sizable bounty if you're not careful.
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