There is deffinatley something strange going on with the calculations Squidward. I paid 5400 gold for 3 levels of high level destruction training and attempted to pickpocket the gold back. Naturally I had 0% success. I used alchemy exploitation to make a potion to fortify chance by 5 MILLION percent ad it was still 0%. I really want to know how these things are calculated. The formula mean.
If each coin was a troy ounce of gold, that's 540 POUNDS of gold. You really think they won't notice losing that much weight out of their pockets?
Gold should be split up into packets inside NPCs' pockets...say 1000G for all but the last 1000G, which would be split into five 200G stacks, and have it re-stack each time you take something out of their pockets. So that merchants' pockets would look like:
1000G
1000G
1000G
1000G
400G
200G
200G
200G
200G
200G
So you could steal the money back, but it would require many rolls.