I get what you are saying, but the first one was his wife of many years. Also, a HUGE percentage of American women are gold diggers, crazy or both these days, so he is not necessarily going for the worst of the worst.
I do think he should leave Florida and maybe take a break from the women for a while.
if I were him it would be Alaska in a small Northern Town that had good internet. Get a job that is low profile and keeps you from dealing with the public.