It seems that each character is exceptionally good at certain things. For example, my current character is really good at evading arrest. For a while I had a success rate of more than 50 percent. My first character was great at stealing cars.
In reference to a previous account, Bubbles said, "One of my characters was awesome at stealing Duesenbergs; I had 27 when I got shot as a Boss."
It also seems that each character is exceptionally bad at certain things. Right now I'm bad at negotiating booze prices and it sometimes takes me as much as an hour to succeed twice.
Other players have reported that some of their old accounts were terrible at busting, negotiating booze prices, evading arrest and stealing cars.