So I figured I would do this achievement since it is one of the few remaining and seemed easy enough (and I have alot of gold now). So I went to each of the nine holds and killed a guard and ran away. Checked the Statistics page and saw that sure enough I hade a 1040 gold bounty in every hold (9 in total), but the achievement did not trigger. So I went to each of the nine again and killed a few more guards, eventually I had about 6000 gold bounty in every hold and still nothing. So I then went and paid off the bounties and got a MASSIVE bug in Markarth, where the guards kept trying to send me to Cidnah Mines, but I had already broken out of there with the forsworn. I was able to fix that bug with a little help from the internet and now all bounty is back to 0, but I am loathe to try this achievement again as it just cost me close to 50k gold for nothing.
The internet seems to reference that non-English versions have some bug with this achievement, anyone else have problems?