Why not get a multiple entry tourist visa which wiill give 8-9 months here each year much cheaper and easier and no need for thai banks or big sums of money. About 150 pounds and mine took a few days in uk
indeed. Always a couple of trolls on social media !. Yes, i always have a small supply in hand luggage for a few days which is sensible. The bulk though goes in hold. Ive had medicine removed at security at least 3 times for the duration of the flight but who knows how its been stored or tampered with whilst its out of your sight for say 12 hours
Obvious to most. Less questions and issues at security particularly in less "civilised" areas of the world and less hand luggage to carry if you use quite a lot of medication.
20 years, flying many many times each year. My suggestion is offered with long standing experience all over the world with zero issues. If your experience is different, thats also fine