Master Criminal

Have a bounty of 1,000 gold in all nine holds at once. Commit crimes (assault, theft, murder) in front of guards in each of Skyrim's nine holds until each hold's bounty is 1,000+ - and don't pay any of them off. Easy way: pickpocket-fail or attack a townsperson in each city and flee. You need all nine active simultaneously, so tour the holds racking up bounties.