Anyone else think this achievement is somewhat backwards? I've been pretty careful about not racking up bounties for my various nefarious activities, and when I do acquire a bounty, I usually just avoid towns until it's worn off. I have dozens of pardons in my bank because I've never really needed them.
I really don't care about the achievement itself, but I wouldn't mind being able to buy some furniture items from the Thieves Guild - but apparently, I need to be a terrible thief in order to do so!