As long as you have the equivalent of bt500,000 in your personal bank account there are numerous ways you can meet the requirements, but having that money is the main requirement.
What lots of people have a confusion about, and speculate on, is not what is going on with this new DTV. Anything new Thailand does, like this visa, and other's, they do not initially make detailed rules. They make it simple, trusting people, then make increases in regulations as they see the exploits being abused, and the perceived loopholes that exist. The one thing they do is grandfather in everyone already on the visa, with the rules that were in place then, or lack of rules then. Anyone on the visa now is grandfathered in to any changes imposed for the next five years. If you don't wait to get it as locations in some parts of the world are tightening up on documentation already, and the length of paid for soft power options. Right now there are no requirements for lots of different details, like no rules you must go to classes, or make doctor appointments, etc, which rules will be made to address that in the future, but won't affect those that have the visa now for the next five years. After that it is different. Don't wait to get this visa, as rules will tighten. As far as tax liability goes, it is no different than being on any short term tourist visa, under 180 days, and they don't care, so for the next five years try not to make them care.
and people have been currently approved too, all over the world, including the Thai embassy/consulates in the US, for the same things you stated. Oh, and I am also a military vet, USAF. Did you actually apply?
so you just started school in November? Immigration doesn't like those kinds of two week vacations from school, whether you have a re-entry permit, or not. In two months you're missing one month of school. In order to get the 90 day extension you must be making satisfactory progress, and attending classes in person regularly. Missing one whole month doesn't meet those requirements. Be warned.
you aren't actually helping anyone. You are simply passing on hearsay that is repeatedly being shown to be false. The so called "expert" you reference actually doesn't know either, and is only guessing. As long as you have the equivalent of bt500,000 in your personal bank account there are countless ways to get the DTV, and thousands are doing it daily.
and by not being legally married to the girl he won't qualify for a type O extension. Remember from his comments. He has no money to meet the financial requirements if he was married.