I’ve been following this topic I’ve the last few years and the consensus seems to be that 3 or 6 visa exempts per year is the limit, and should one try to exceed that, they get pulled to the side for secondary questioning and possibly not allowed into Thailand, or worse, sent back to wherever they came.

 

My situation is different. I work in Hong Kong and kids go to school in Samui, live there during the school year, and leave on breaks. I have a European passport that gives me visa exempt entries.

 

For the last few years, I fly direct from Hong Kong to Samui pretty much every Friday and return to Hong Kong every Monday. 90% of the time I stay 3 days, occasionally 4 days, once or twice up to a week. And 90% of my entries have been at Samui, a few others via BKK, never by land. Add to that for bigger holiday periods, usually Christmas and Easter, I make no entries at all for about 3-4 weeks, and over summer I make no entries at all for about 2-1/2 months.

 

I've never asked for 30 day extension. I’ve never stayed more than 2 weeks at a time, usually in and out over a 3 day period.

 

Should I expect one of these days that I might be denied entry and sent back to Hong Kong, or asked for proof of funds?  I’ve never been asked any questions other than once when they asked, upon leaving mind you, if I had wife and kids in Thailand.

 

Should I consider myself lucky or is this normal and should be expected because I come and go so often and typically only on weekends that I do not fit the profile of someone illegally living or working in Thailand and therefore not subjected to additional questioning?

There no real limit on visa exempt entries.

Your short stays will not attract attention as you have already experienced. It is mostly people that stay for the full 30 days that get questioned.

No one can guarantee anything. However, I cannot imagine a rational immigration official ever having a problem with your pattern of entries. The only reasonable alternative would be a multiple entry Non O visa to visit your kids (assuming one or more has Thai nationality).

It's the time spent in the country rather than the number or entries that really count. I have a friend that works in Cambodia, flies into BKK every Friday, stays for the weekend, and flies out again on the Monday. He has been doing this many years, always enters with visa exempt, and has never had a problem.

 

I doubt you'll have a problem either, but there is always the possibility of getting questioned about your reason to visit so often. It might be worth carrying proof that your kids live and go to school in Samui as that should be sufficient to satisfy even the most officious IO.

It depends on how long time you want to gamble.