Making the jump to BKK in May, so many questions

Hello Group!


Will be making the jump to Bangkok early May 2024, and am in the thick of heavy prep mode as I type.  Some quick background, I am 59, recently divorced and semi-retired.  I'm selling my house and my plan is to go to Thailand and SE Asia in general for 9 months to recharge my batteries in a lower cost of living area, wait out a non-compete and pull the pieces together to launch my next venture back in the States Q1 2005.


I will visit the local Thai consulate here in Portland, OR next week to explore an extended one year visa or seek the best options given my circumstances but very well may end up going on a 60-day tourist visa, get a one-month extension, then visit Vietnam and some of the other countries in the area either for a month at a time or as visa runs, finally going to India to get some software written and a website built before I go back to the US.


Thinking of renting a 1-bedroom condo in Sukhumvit, Siam or Thong lo (open to others too) for one or two months of then figuring out next steps from there. My preference is a high-rise building with pool and gym.


Been watching tons of videos and reading lots of expat material but still have lots of unknows I need to learn so here are a few questions for the community.


1)    Are there any specific buildings in the above-mentioned areas you would recommend looking at for renting?   $1500 USD or less, less is better of course.


2)    What international health insurance do you recommend?


3)    What banking savings/checking/debit/visa from the US do you like to use as an expat or digital nomad to save on fees ease of transfer? I currently use Chase Bank.


4)    I will be selling most of my household goods and vehicles vs putting them in storage. I will be bringing one checked bag, one carry-on bag, and a daypack.  What would you suggest I pack to bring with me for an extended trip?  What do you suggest I don't bring as I can easily get it in BBK?


So many more questions but this is a good start.


Thanks in advance, Jim

Opps typo in BKK in title. Mods, if you would be so kind to edit the title.