I know a guy who also is working abroad (offshore). He is younger then 50 and he got himself a elite visa. But that was when it was much cheaper.
If you would normally could get a Non O multiple then you can still get a Non O 90 days single entry in Thailand and get a yearly extension and add a multiple reentry permit for 3800B.
DTV is not about rotations such as offshore work. Its about doing remote work while being in Thailand for a company outside Thailand and doing no business in Thailand. There are also soft control options such as long term medical treatment etc.
You did not get any visa. Its visa exempt. Meaning NO visa. And thats the point. Stetching the limits and you will be denied or at least be told to get a proper visa.
You mean that at the first 1 year extension you can not use the monthly transfer method. Thats correct. But still many embassies profied verified income statements.
I do the certified income statement from my embassy for the last 7 years. Never is there any word about only accepted the first time. I guess you are incorrect in your statement. And there are still plenty of countries who issue a certified income statement. I know the US, UK and Australia don't.
If you are only here for 2 weeks and also going to stay in a hotel i would not bother to do a TM30. You are not going to do any business at the immigration. But its the law. So up to you.
As a tourist its no concern for you to have been repprted TM30. Only if ypu want a 30 days extension your local immigration might ask for it. That would only be the TM30 of that moment. No history check