Not for the “soft power” category apparently : 2 guys I know just switched from retirement visa to DTV soft power with only 1 dental appointment in a clinic in Bangkok. When people say rules are getting harder it’s only because they read comments from people applying in some “difficult” embassies. Some embassies are very strict, some are very easy . Just choose wisely and you can get soon a 5 years multi entry visa with zero hassle. Now we have enough feedback: absolutely nobody with DTV (including the soft power category based on a 1 week cooking course) got denied entry after a border run (6 months ago stamp per entry). Rinse and repeat. For 5 years 😛
It’s a no brainer : get a DTV !!! Far less paperwork , no 23k US$ to be sleeping on a thai bank account for the time of your retirement visa , no yearly extension (with retirement visa you have to extend it every year: lots of paperwork every year AND you have to be in Thailand to do it: you cannot travel outside Thailand when it’s time to extend it) !!!
I don’t know where you live but where I live in Thailand you can be sure that if you, as a Farang, don’t wear an helmet while driving a motorcycle , you will be stopped by police and fined. While a Thai family of 3 on the same motorbike with zero helmet just in front of you, won’t … So the police does enforce motorcycle helmet law … but only for Farang … Might be the same for tax laws enforcement … and it would be super easy : they just need to link taxes and long term visa extensions.
Moreover for Thai tax residents (you will become one if you stay more than 180 days in a calendar year) there is a new tax law in the pipeline to tax worldwide revenues . And not only money transferred into Thailand . Google « Thailand tax worldwide revenues » and you will see the whole picture.
And to answer your question: no insight on taxes offered whatsoever.