You can enter the country, but your application MIGHT get rejected or void if they find out you were in Thailand. It's not 100% certain, but, it's a risk you need to assess. It has happened to several persons already (while some others did the same and had no issues).
No, working as a contractor is OK. I got my DTV this way. However, my company wrote a letter addressed to the local Thai embassy stating my start date, my position, my job description, my average monthly salary etc. It was signed by one of the big bosses of my company. Embassies live old fashioned stamps on printed (and later scanned) documents. Just originally digital documents (rather than scans of printed documents) aren't much well received.
interesting, South Korea also has the equivalent of that blue book you mention (although now everything is digital, no actual books anymore) but you can get in it only trhu birth, adoption, or marriage. So, no girl/boyfriends or friends, etc.
A. Nony Mous frequent visits are ol for the so-called digital nomads. Now, if one is supposedly attending a soft power course, it might rise some eyebrows.
I enter and exit very frequently, zero issues. That's what the visa is for (workcation category here). Now, if it was granted on soft power, it MIGHT be different.
he's not whining. He's just giving a very good piece of advice. Don't put all the resources in a single account, in case something, even temporary, happens.