Never had any issues with Emirates bu Qatar were very officious, asking a lot of questions, this was a few years ago.

Just go with the Non Immigrant O based on "retirement". As advised, see a visa agent.

Insurance is for the car in Thailand, not a specific driver.

Obviously you mean September 24 or your trip has got off to a bad start ! Whoever gave you advice about the visa waiver or 60 day not being suitable was wrong, not many other options available, 60 day would give you more time, but with an agent it is possible to get things sorted in 30 days if the process is started immediately after arrival.

No requirement for documents from home apart from your passport.

Many options, depends on how long you are staying, nationality and possibly even age.

Free VPNs might be OK for casual internet browsing but useless for streaming TV. Nord or Surfshark are only a few £ or $ a month, they always have discount codes available.

In the pocket of the CCP.

@Joe *****

recommended, used by many expats. Soi Post Office, (Soi ), literally opposite the Post Office.

Irrelevant what visa you are on, TM30 applies to everyone but as most tourists stay at a hotel they sort it out. As Brandon states, if planning to stay beyond your 60 day TV meaning a visit to Immigration then best to sort out your TM30 to avoid a fine, if going home within 60 days then you should be OK.

@Mark ******

booked mine about 2 months ago.