What is the best way for my family to live in Thailand for 6-12 months while managing visas and work for my daughter?

Okay I feel seriously overwhelmed trying to sort this all out. I have a family of 4 - myself I’m almost 50, wife is 37, kids are 15 and 18. I primarily make my income off of investing on the OTC and a very small trust check monthly as well. My trading account tends to have $100k or more liquid and $200-400k in play. We own a home in the US we plan to rent out while we aren’t there.

What is the best, simplest method to live in Thailand for 6-12 months at a time leaving to either another country or back to the US for a few weeks to a month or so annually?

My daughter being 18 would like to work there but my 15 year old will be continuing digital classes via a US school. I will continue to randomly swing trade while the wife will not work.

Best visa course of action with the process to get it done for a person who hates paperwork and really isn’t too great with crossing t’s and dotting i’s 😂