There was a TV show in Japan where a man had to stay in a room until he managed to win $10000 of value in sweepstakes. I wouldn't say you can make a full-time job out of trying to win sweepstakes, since he ended up staying in the room for about a year.
https://en.wikipedia.org/wiki/Nasubi#Denpa_Sh%C5%8Dnen_teki_...