A little background... I lived in Chiang Mai for a total of 4 months which is not nearly as long as 1.5 years or as long as others have stayed there. I lived there completely legally and got the correct visas to do so. I am also still travelling the world and am 8 months into the trip after selling everything I own.

So, should you give up your job to move there? First you want to ask yourself why you want to move there? Yes standard of living is great and it's cheap but why do you really want to move there? Do you dislike your job? Do you want to make it on your own? You seem like a really smart guy so you should take the time to really think about what you want to get out of this move before doing it.

If you want to be a digital nomad and work for yourself it may be a good idea to work on a MVP (Minimum Viable Product) in your albeit limited spare time to see what interest you get in your product before leaving.

The next thing you want to ask yourself is do you want to move so far away with so many ties back home? 2 rental properties and student loans are hugely restrictive and ultimately you are responsible to look after them/pay them off. Would it be worth selling your property or handing them to a reputable agent to look after? Also is it worth using your savings to get rid of the loans? You may find it more comforting to leave work and move to Thailand knowing the cash you have is 100% yours.

I'm not trying to dissuade you. What you're considering is a huge decision! Just be careful to make sure all loose ends are tied before taking the leap.