I am thinking of applying for a DTV using the workcation route. I am not in a big hurry and requesting first hand information from people who have applied for DTV from the USA (Chicago embassy).

I have a website that makes around $500/month from Google AdSense. I'm stashing that money into a separate HIS account, and now it has a little over $16K USD. I don't use the money for my living expenses.

I'm also a so-called 401(K) millionaire, and every two weeks I sell around $4,000 of VOO shares for my expenses, and I will continue to do so till I get my social security at FRA in 2028.

I live four months in Thailand (not continuously), four months in Portugal, and four months in the USA. I have a house in the USA, a condo in Thailand, and an apartment in Albufeira (Portugal).

For my business, I file US tax as a sole proprietor along with my 401(k) withdrawals. I have ACA health insurance that covers 50% of my emergency expenses anywhere in the world.

At present I use an agent assisted non-O retirement extension with a reentry permit costing me around 17K baht/year

Is it prudent to get a DTV, and if so, how should I proceed? For example, set up an LLC, a state registered company, or anything else. First hand experience is appreciated.

When I retire here next year, will my US pension and Social Security be taxable in Thailand? Will I be paying Thai taxes and US Federal taxes? I guess at least I won't pay colorado state taxes.

Learned this from a CPA friend of mine...

If you are American and have a foreign bank account - you need to fill out "FBAR, *Form* 114" with your taxes yearly, or ELSE! There is a $100,000 fine that may be leveled against you, if you don't. Look it up - don't find out the hard way!

Any US Taxpayers have a Thai wife, married in Thailand.

Do you get to claim her as a dependent?