Depends on how much the customs officer on any particular entry likes the look of you. Your friend is probably better off getting an actual tourist visa. He'll run into trouble using his current method eventually.
I left a couple of weeks ago. No plans to go back with the current situation. Plenty of other countries that are less hostile to foreigners. Hopefully the military steps down next year, like has been announced, and the madness ends.
It's 2017. Who uses cash anymore?? Cash is only good for street food and hookers, but oh wait, the Thai government is in the process of shutting those businesses down.