@Radost *************************

Yeah. I didn’t. I am on my 3rd 2 year license. That is how Chiang Mai DLT handles it, unfortunately. But I heard some reports of DLTs in other districts handling it differently. Wouldn’t surprise me. After all, even immigration varies from province to province or even office or officer. I think it is annoying.

@NT *******

You should use a reputable travel health insurance from your home country. Why? Because it is much easier / more familiar to enforce it should you ever need to. I feel sorry for people from the US needing to pay rediciulous rates for such insurances. But as a EU / German citizen, I get unlimitted health insurance abroad for up to 5 years for as low as 50 EUR / 2,000 THB / month. This one, I can highly recommend if having a residence in Germany at the time of signing:

@Andreas ********

Yes and no for Europe. Annual contracts are indeed only intended for short term trips (usually between 30-90 days each) - that is why those contracts are dirt cheap. But then there are contracts for longer trips (up to a year / or up to five years). Yes, for those contracts one needs to have a residence in that country - but not during the whole time, but only at the time of signing the contract. With my German insurance for example, I can even have that contract for the maximum time possible, and they will refund me the difference should I return early. Thus I always make use of that and have that contract run much longer than I intend to travel. And the best part (sorry US guys): Unlimitted coverage for as low as around 50 Euro or about 2,000 THB a month. Highly recommended, should you live in Germany:

Bear in mind that you will only get the 5 year license (at least in some districts), if you are on a long term visa. Else, some districts only issue 2 year temporary licenses again and again. Of course it is different everywhere for no reason - like always in Thailand.

And don't listen to people sugegsting to not be needing any health insurance. Yes, simple tratments are rather cheap in Thailand. But should you have a major exident, the bills could ruin you - or you would have to settle with less then the best treatment ... and who wants that?

SafetyWing allows you to buy while already abroad - there is better / cheaper options before traveling, but few that allow signing up while already traveling:

If you meant border bounce: yes. If you really mean visa run: no. Quote from their website: "Visa processing will usually take 2 business days. Visa collection will be the next working day by walk-in."

I never had the chance to check out Hat Yai (other than passing through, really). On paper it looks like it could be the "better" Chiang Mai. Not sure about the state of infrastructure and good schools, though. Google suggests one, though:

@Andreas ********

True for cost of living. True for not being exposed to the overtourism negative side effects. But lack of good education (international schools) and some western comfort infrastructure might be an adverse effect. Also, even the Isaan is affected by periodical unhealthy weather and pollution conditions.