Is it possible to repeatedly leave and re-enter Thailand on a visa-exempt basis without being questioned?

Was offline but what he said

On my WAY.!!!

You clearly come from one of the 90+ countries that show up here and get stamped in for free for 60 days on the visa exempt program

You get 60 days when you enter, you can extend that one time for 30 days at the immigration office where you stay for 1900baht

While there technically is no limit to visa exempt entries (by air or land) what you won't be able to do is live here long term on them. Even with having proof of where you stay (which if anything only shows you're NOT a tourist at all 😮 )

Sooner or later you'll get called out on it, questioned by passport control and denied entry.

I'd say you could probably fly in get 60, get the 30 day extension, use a service to bounce you out and back at the border to get a new 60 day entry stamp, get the 30 day extension and probably be able to use a service one more time for a 60 day entry and 30 day extension after that but that'd be pushing it and maxing out you milking free entry to 'live here'.

Staying in cambodia a couple days isn't gonna fool the officers at passport control into thinking you're a 'real tourist', they'll know all you're trying to do is get a new free entry stamp which is why I said "use a service to bounce you out and back". Post on a group where you will live and ask for recommendations of ones in your area