Just a thought. You talk about properties bringing 5k a month rent. Why not keep your property and rent other out. Even if you still have a mortgage to pay out of the rent you will still have that asset for the future?
If you come on tourist visa apply for the METV (Multi Entry Tourist Visa) while in USA. With good planning and "Safe" border crossings it can give you over 8 months in Thailand.
The first thing to look at is the cost of a decent school for your children - you did say you might send them there in the future. The costs are often a nasty surprise to those that do not know the system. This is especially so if you want them to follow a particular country curriculum for University entry etc
So many grey areas. What about people coming in to present at a conference or meeting (Public or company in-house). What about coming in to deliver training to company staff or even to outside people working on your projects. Can it be done on VE or do we need a Business Visa - do we need a temporary WP (They exist). Company I worked for went through all of these questions with lawyers as have many others. Pretty much a blind eye is taken as to strictly apply the letter of the law would be detrimental to smooth operation of business in Thailand.
Of course not - even companies who say they do it often do not. Nice publicity for the C-Suite to tell people it is what they do 🙂 Public bodies even less so.
It is not rocket science. Make a strategic plan. Then execute that plan ie the projects in the portfolio. Make sure you are on track and if not correct or pivot. Track using something like OKRs against each initiative :-( I have gone all corporate there lol
Anonymous participant 844 There is no doubt many are openly working in Thailand on DTV when they should not and really need Work Permits and different visas. Some are even quite blatant about it and promoting services on Facebook and TikTok.