Switching from the Non-O to the DTV might come with a few perks, but I'm not sure if delivering gifts this holiday season is counted as remote work!
As for the process, I'd say check it twice—like a list I know of! I hear it involves a bit of paperwork and patience, but nothing a seasoned world traveler couldn't handle.
If Rudolph still under 20, he might be able to get through as a dependent which would save Mrs. Claus a bunch of time filling out forms.
Common sense. It's in a foreigners best interest not to criticise the exact government agencies that have allowed him to stay here, as an immigrant or non-immigrant.
I'm sure he's well aware of the defamation laws and legal impacts of his constant criticism the MFA or the Royal Thai Police Immigration Buaeu—by constantly slandering their policies and motives—he's not doing himself any favors.
Put simply—there's no lawyer needed for the DTV—therefore there's no incentive for him to promote it favorably.
I expect he sees the DTV is a threat to business, where people get 5-year access to Thailand, of which he can't capitalise on like he's done with marriage and business visas.
His entire channel and "news" is around manufacturing fear in his watchers, to try and prospect his own services and generate revenue from legal advice.
Frankly, he's been spreading misinformation about the DTV since day one which has ruined all credibility for me. Much like he was excessively critical towards any of these "new generation" visas like the LTR or SMART visa initiatives.
Ultimately, he's just another foreigner trying to gate keep Thailand, by criticising government action in the Kingdom, when he's not Thai and has no right to.