Is the basis of easily getting money is to pickpocket shop merchants - save first, then pickpocket, etc.?
Then buy equipment/ammo. Will he restock next day or do I have to find another shop merchant in another town, etc?
Doing some quests or farming random encounter seems to be faster than save scumming for pickpocket.
And i think most merchant only restock every few months.
Just boost gambling to 120%, with luck of 10 and hit the tables in Reno...find a $100 bet and hold down the corresponding key with a weight, and come back in an hours time. You should have several million bucks...