It depends on the cost of the item. If it's something cheap, you should be able to swipe again withing an hour or two but if it's something expensive like a computer, tv or pricey painting, you have to wait about 8 hours. I made a family of three thieves. They like to go on crime sprees. One person would chat with the owner of the house or create some sort of diversion (fight, tell a group story, etc.) while the other two robbed them blind. It was a fun series but when I went to play other families in the game, I was a bit annoyed that all of their electronics and paintings had been stolen, lol, but that's life.