I would just wait the month and go clean. His mom has a business so he could learn the job and later run it himself. But fucking this dude up is fair, he just need to control himself so he dont get cracked open with a rock again.
Considering how this "game" works, he really may as well do anything. I'm kinda surprised though that he still gets immersed in each life, pretty much unwillingly. But I guess that's just normal.