This can be done if e.g. the other country turns you away. But generally you have a lot of explaining to do when you stamp back in, I wouldn't recommend it as something to do regularly.
Thai banks are getting stricter about accepting large sums of money from abroad. I suggest you open a Wise account and slowly transfer your money over a bit at a time, don't try to do it all at once or it might get impounded.
Antihistamine cream works a charm. It's most effective if you put it on as soon as you notice the bite. The brand I use is Anthisan from the UK, but there's probably something similar in Thailand if you ask around
From memory, it used to be possible to get an entire villa on ASQ, then (and only then) you were allowed to use the pool. If you have extra $$ to spend and really want that pool time, I'd check if this is still an option