My current visa and work permit will expire this month. I’ll turn 50 in about 3 months and want to switch to a retirement visa. What can I do for a visa during this 3-month gap? Can I travel out of Thailand (and back) 2 or 3 times with a visa-on-arrival until I turn 50? Can/Should I apply for a tourist visa in a neighboring country? Malaysia or Singapore would be easiest for me - will they be hesitant to grant a tourist visa to someone who has lived and worked here several years already?

Any recommendations for a visa during the 3-month gap between Visa/WP expiring and turning 50yrs old?

Tourist visa should not be a problem, or just visa exempt if you have to. Remember you will require a non immigrant O visa for retirement extension of stay or convert with about 15 days remaining at immigration and at that time will have to have proof of 800k in bank or income of 65k.

Thanks for the reply, loburi3.

I'm aware of the 800k in bank for 3-months prior. Will work on getting that in order.

But I don't understand your statement, "Remember you will require a non immigrant O visa for retirement extension of stay or convert with about 15 days remaining at immigration...."

...I feel like such a dunce now......If I get a tourist visa, I can convert it to non-imm O for retirement at immigration?

Depends on your birthday - if you still have 15 days or more remaining on a visa or visa exempt entry it can be converted to non immigrant by immigration at large places (always by Bangkok if not your office) for 2,000 baht and proof money in account (does not have to be any time period).

Also first extension of stay for retirement only requires money in account 60 days (not 3 months).

Great info, Lopburi3. Thanks for your help and clarification.

Appreciate the correction about the money timetable, too.