It is sort of an edge case. But what isn't with Thai immigration. Many of their requirements don't exactly ever meet the real lift situation of applicants. Good luck.
Sure. During this eVisa process, they will make you upload proof of residency in the UK ... just upload your UK driving license. That should make them think they are responsible for you. eVisa in Italy might go through as well (given the address in the bank statement). But I would guess UK is the safer bet in this case.
Almost. But the METV gives you 60 days, each (on every entry). So, if you were to leave and re-enter a day before it’s expiry, it would give you 239 days. With one final extension then a day short of 270 days.
Wrong country, if you are looking for reasonable explanations in matters of bureaucracy. Either play their game, or beat them at their own game. If the obstacles get too much: find away around them - there usually is.
So, the question then is: How / where to make copies of all passport pages after being stamped out of Thailand, but before stamped into a third country again. 😂 Visa application „on the fly“ so to speak. 😂