If you're going to be in and out a couple of times and spend time outside Thailand (not just a day or two) you'd be better just just leaving and re-entering on visa-exempt basis and getting 30 day stamp each time which can be extended a further 30 days. Keep in mind if re-entering via a land border you can do this only twice in any calendar year
Do you need an excuse not to learn the language? It's not compulsory although it's very useful. I wouldn't be comparing Thailand to the dysfunctional USA
No problem at all. As soon as the money hits your account and is recorded as an international transfer you can do whatever you want with it. I do it all the time. I immediately pay my rent and internet, and within days the electricity bill is paid. 10k immediately goes into my lady's account for the monthly "market shopping" which she excels at. Immigration don't care where it goes, only where it comes from.
People will give answers based on knowledge, experience and hearsay of different immigration offices. It's important to understand that just about every immigration office operates their own policies (within the legal structure) and advice from your office has more substance than advice from a Facebook group.
This might sound like a dumb question but did you consider asking the staff at the immigration office if you could delay getting your extension stamp until the 18th?