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.