Will repeatedly using visa exempt entries and 30-day extensions lead to problems with Thai immigration?

I think what you are trying to ask is if you enter Thailand visa exempt and extend for 30 days then you leave for 2 months and repeat will you have issues? While the ultimate decision will be down to the immigration officer you stand in front of if you keep repeating this you are eventually going to run into issues. Twice will be fine, you might get away with thrice. I can't see it going much further

It is solely up to the Immigration officer in front of you.

If you know upfront that you will stay longer than 30 days, the best solution is:

When going to Thailand for 31 - 60 ( 90 )days, the 60 days touristvisa is the best option.

It is cheaper than visa excempt + 30 days extension.

No need of a onward ticket ( 90 days 1 onward ), if returnticket within 60 days.

It is easier to apply from the comfort of your home.

thaievisa.go.th

If visiting the nearest Thai Embassy website, you may find informations, that make it much easier to apply online.

Not wasting holiday time to find, go to and waiting at a immigration office ( 90 you would need that ).

Then no need to leave Thailand in up to 90 days.

Larry Far. There has never been a 30 day visa on arrival. Passport holder from select countrys can pay for a 14 day visa on arrival. Many other passport holders can receive a "Visa Exempt Stamp" when they arrive. This is not a visa at all.

Two maxed out exempt entries per year should normally last.

Visa Exempt entry is still 30 days so your was is incorrect at this time

Visa on arrival has never been 30 days. Visa on arrival is a 15 day VISA that you apply for and pay for at the airport, available to only a few nations like India and China.

Visa exempt is a 30 day stamp (it's not a visa, you are EXEMPT from needing a visa) that you receive if you are from a list of countries and arrive without a visa.

Visa exempt is eligible for a single 30-day extension on each entry. If you enter and get an extension, and leave Thailand and enter again and get an extension, you will not have any issues. That is only 2 entries and only 120 days. 3 would probably be okay but they might question you at the airport, but I've never heard of anyone having issues with just 2.