Philippines is one country that I'd very *tourist* friendly. Ex-pats can stay long time. Malaysia gave me 90 days without asking (VOA). Not sure of other countries in SE Asia.
Nobody is trying to "game" the system. If tourists are spending their money in Thailannd we are helping the local economy ! Ask the local hotels and restaurants and tuktuk drivers. Make it more affordable to get a "proper" visa
Most likely true in this computer age ...if he was flagged. But why return to passport country ... he could simply go to Laos and practice Laotian Muay Thai or Malaysia. etc ?!
On the one hand Thailand promotes tourism ... a 6 to 9 mo visa would follow. Whether I'm "living" or a "toyrist" I'm still contributing daily to their economy. But I also am mindfully we are all just guests in their country.
I've even over stayed my extension 2 different times. They weren't happy but nothing about not allowing me back in (just pay fine). Knock on wood most agents very nice at land crossings especially compared w attitude you get from usa customers agents.