The biggest thing that stands out is the fact that his rent is paid for by someone else. I can say that this is sapping him from a lot of motivation to get out there and work for himself. He probably knows that once he does, that will stop and may never be that way again. That's not an excuse, just something I think is a fact about why he's being "lazy" about getting a job. I know that doesn't help.

Thing is, it may take him a long time before he really wants to get out and work for himself. he may have to face losing his caretaker's money before he'll do that. Can you wait for that?

On the nagging side, you're not nagging. I don't see it that way at all. You expecting him to work is fair. But I will say this. You probably won't light a fire under him by asking him or telling him to get a job. You can't make him do that. I say this to save you the pain. Since you can't change his ways, just let it go and save yourself the aggravation and being yelled at. The choice, IMO is to move on and wait for him to get his life in order before taking him back or stick around and pray for tons of patience.