Is it wise to use a visa exemption for multiple visits to Thailand or should I apply for a tourist visa?

It doesn’t matter if you enter multiple times on a visa exemption or on a tourist visa you bought outside of Thailand

Having been in Thailand visa-exempt or on a tourist visa doesn’t cut any ice, in regards to your collection of “touristic entries”

*** In the end it is the Immigration officer at the border, who will do a quick count of how many days you have spent in Thailand on “touristic entries” within the recent 365-days period

If he counts more than 180 days, he might think you are abusing the tourist entry system for a long term stay in Thailand. He might pull you aside and starts to ask question like those:

*** “do you have any proof of onward travel leaving Thailand within 60 days?”

*** “which are your intentions in Thailand? Do you have a girlfriend, do you work ?”

*** why don’t you buy the right visa for your purpose of visit?”

If he would really start looking for a reason to deny entry, he would ask you for a proof a funds which you need to carry on you in the form of CASH money bills.

The official requirement is that you must carry cash of the equivalent of 20,000 THB when you want to enter Thailand. Credit cards are not accepted as proof of funds.

*** this, you should know and have run a calculation by yourself of the total number of stay days in the recent 365 days, so you know what to expect.

*** some people will tell you they did 7 or 8 visa exempt stay within a 1-year period. However they don’t tell you that each stay never got maximized to the full extent of 60 days, and never got maximized to the 30-days touristic extension for 1900 THB. They obviously had only accumulated short stays, and Immigration officer can see it by your stamp history.

Many of these people are roll-on, roll-off oil platform workers who like to spend the leisure time off work in Thailand, and if questioned by Immigration, they can show proof of what they do.

*** So it is all coming down to the question: Are you a “real” tourist, or are you just looking for a way to spend as much time as possible inside Thailand?

If you like to visit thailand as.much as you do and you dont want a non o retirement visa then I would suggest you look into a DTV soft power 5 year visitor visa which allows 180 days stay per visit so you can come and go as much as you like without the concerns you raise.

New calendar year next january starts a new count. You will get a visa exemption. Have a ticket out and some usd on you. You will get 60 days. No problem.

Maybe the single entry 60 day TV for the May trip as you suggest. At January you will be ok as not much time spend in country at that time.

METV (6 months) likely avoid less questions although I was still asked once 2+ years back for proof of exit at BKK which would normally be an airline request if any. It’ll give you 60 days each trip with option to extend 30 days per entry so could actually work out to c9months. took up to a week from application if I remember correctly

Just apply for a multi entry tourist visa

I

You don't sound like a "real tourist", so you better convince them (not me, I have no say on this) that you're a tourist, if you want to enter as one. If they don't believe you're a tourist, even having a METV won't guarantee your entry into the kingdom next time.