Anonymous participant but your DTV is attached to the other passport number. When entering on the passport attached to the DTV, there is no need to include your other passport. Very different.
Anonymous participant 424 - then you have me, who has DTV for mobile work, who is still interested in signing up. However, you can make the same argument with any course (cooking, muy Thai, etc.).
Anonymous participant - Ideally you probably should have booked a short term place (just a week) initially. However, it might look even more strange to change it now. Just have to lean into it and be honest. Try not to focus on the fact that he is your boss, but if they catch it, be clear. Can you highlight that while he is your boss, he is a friend and that is why you live together (only if they ask questions)?
Anonymous participant - Remote work usually means you work away from your company office. If your company only has one other person and they are in Thailand and you are living and working for him, you can see how the embassy might not consider that “remote work”.