I am a 77 year old Australian living in Chiang Mai, Thailand for over ten years. I self insure for medical. I have a reserve in my bank account to cover at least one month hospital costs in a private hospital. If that proves insufficient, I would attempt tp fly back to Australia where my medical treatment would be free.
As long as the Immigration officer, after reviewing the posters stay history, accepts that she continues to be a tourist. Otherwise he will deny her entry.
If this is your third visit within a 12 month period, the Immigration officer could easily believe that you are no longer a tourist and could deny you entry unless you have a visa valid for the reason of your stay. Be warned.
1. Yes, I suggest that you apply before arrival. 2. Once you are here and have your Retirement visa, then you can go to Immgration and purchase a single or a multi re entry. 3. There is no m inimum stay requirement. 4. It is straight forward and simple to do yourself - why pay an agent extra money.
I am confident that the Thai police know and understand the laws relating to licences from ASEAN countries which are totally different to the laws for licences from Western countries.