This is the main way I have heard of people doing it. I should probably get involved with it again soon before it's ever patched out.Sadly the o ly way to get it is from selling stolen stolen stuff.
You can do this fast if you group up with someone and have them spam aoe in that gambling spot south in Reapers March, and the rest of the group picks up loot. This way you won't get a bounty at all, unless you sre the killer.
This is the main way I have heard of people doing it. I should probably get involved with it again soon before it's ever patched out.
My favorite is the houses outside above the TG in Orsinium, it has two pretty empty houses.
This is my fourth time getting this acheivement and mainly I stick to the streets and houses of Wayrest. Over time I've created my own route that I follow (or at least try to because I am a lazy piece of gunk) every day.
This one knows where she is going tonight.Actually the easiest and most risk free place you can steal a lot fast is the port in Daggerfall. The 2 ships anchored there have a lot of containers in the cabins, bay and even on the deck which give plenty of blue and green stuff to sell. I trained ledgermain on 3 chars there with 0 bounty.