rkh_

Entered Thailand last week for the second time on a DTV. After presenting the immigration officer with a printout of my visa paper, she spent about five minutes carefully reviewing each stamp on each passport page. She then asked "how long do you plan to stay this time?" At the time I felt as if a reply along the lines of "54 months with biannual extensions and border runs" would have been the WRONG answer. So I said "6 months" and was allowed to pass. Definitely left the immigration queue with the impression that immigration is skeptical of the DTV visa.

I work offshore half the year and live in Thailand when not working. Having a proper long-stay visa like the DTV is a huge benefit. For example, landlords will be more receptive to renting to you. It'll be easier to get a bank account, driver license and an auto. For US persons a solid visa is a de facto requirement to claim tax breaks like the FEIE. For the DTV, I would advise you NOT to apply under work-cation/freelancer status. Even if you could get an employer letter approving remote work, The risk is that the person evaluating your visa application may correctly determine that you are not actually going to be working in Thailand and deny you on that basis. Instead, apply under whichever of the soft power categories is most interesting to you. The bar for qualifying seems to be very low for all of them.