Just arrived on Thursday morning to Chiang mai from US on self employed workcation with US passport, here’s how it went:
Filled out digital arrival card at immigration, put 180 days stay on it. As soon as I turned around, an officer approached me and asked me to sit for an interview.
I was visibly excited with a big smile and was respectful & honest about my intentions.
We sat down and he with a younger officer started to ask me simple questions.
The older one was testing my Thai (I have barely any) and asked where I was staying, what I’m doing here. Very friendly and was watching my reactions closely.
I said I love Chiang mai and the north so I’ll stay in a hotel and look for a condo/house to stay more long term throughout my DTV. I said I will be coming and going over the 5 years.
I said I’m working here remotely and that my work is mostly on the ground in Colorado + remotely running the business here. I said clearly that I do not work in Thailand, that I earn remotely from abroad.
The younger guy was filling out a form that with my passport, visa, and hotel information.
He asked to see my proof of funds - showed him my savings in my banking app. He asked if it’s physically accessible - I said I can transfer to my debit and withdraw from ATM anytime.
They asked how long I’m staying - I said the full 180 days and that I will spend as much time as possible in Thailand over the 5 years, with a big smile :)
They were satisfied with my answers and gave me my passport plus that form they filled out and walked me to an immigration officer to get stamped. He was also super friendly. Barely said a word, scanned my fingers, took my photo, stamped my passport for 180 days (I checked carefully), I thanked them and walked through.
The whole experience was so friendly and I just did what I was asked with nothing to hide.
Hope that helps.
I will also add that I was in Thailand on 60 day tourist visa + extension a couple of times between November and June. I returned after 6 weeks in US with my DTV.