There are 9 main locations in Skyrim, and to earn this trophy you must simultaneously have a bounty of 1000 gold in all of them.
They are:
- Solitude
- Morthal
- Dawnstar
- Winterhold
- Whiterun
- Windhelm
- Riften
- Falkreath
- Markarth
The method I found was fastest and easiest was this:
- Save your game (not quicksave or autosave, but actual save)
- Pick a hold, fast travel to it.
- Kill a guard or civilian. Really doesn't matter because you're just going to load up your old save after you earn this trophy anyways.
- After killing the person a notification will appear in the upper left corner letting you know you have a bounty of 1000 gold added to the current location.
- Run away from the town. As soon as you are far enough away to fast travel, do so.
- Repeat for the remaining 8 holds.
- Once your trophy pops, load up your save and continue the game as you were before you decided to earn this trophy.