Are you actually on the 90-day non-B visa, or are you on a 1-year work extension?
If you're on a visa, you cannot do anything except leave without a re-entry permit to cancel your entry stamp and then apply for a new non-O visa either from a Thai embassy outside of Thailand or from your immigration office after you return as a tourist, if your office allows conversions to non-O inside Thailand. This is because the first extension must be for the same reason your visa was issued for, so you cannot apply for a marriage visa or marriage extension from a work visa, you can only apply from a work extension to a marriage extension.
completely wrong. The airport is MORE of a problem. Hundreds of people per week are denied entry in Bangkok alone. And at least at a land border you can just easily return to the country you were entering from. At the airport you're put into detention until you can pay for a ticket to where they tell you that you have to go.
No one can give you an answer because it's up the immigration officer you're standing in front of. If they don't give you a warning the 2nd time, you'll probably be able to enter the 3rd time because they usually (not always) give you a warning before denying entry. Just make sure you have the cash requirement for entering as a tourist which is 20,000 baht or equivalent in another major currency in cash. And also have your flight ticket out of Thailand printed and available.
If they pull you out of line, expect to be interrogated for 30-60 minutes.
Yes. The 12 month statement is a base requirement for the extension. The credit advice is supplemental documentation that works on top of your bank statement to show the source of the funds.
I've seen the same report from others before. That once you change passports, you cannot use the online system until you leave Thailand and return. Doesn't really make sense, but what does in Thailand?
You didn't miss anything. A 90-day report is for reporting 90 consecutive days spent in Thailand. If you were not in Thailand, you were not spending 90 consecutive days in Thailand. When you return to Thailand, you start counting again at day 1, because it's only 90 consecutive days spent in Thailand.
When you go to get your extension, they might do a new 90-day report for you, and they might not. If they put a slip of paper in your passport that gives you a new date to report for your next 90-day report then they did one for you. If they do not put any paper in your passport, then your report will still be due 90 days from the day you entered Thailand.
Completely depends on your immigration office. Most want a new TM30 every time you re-enter Thailand. Some even want a new TM30 every time you travel within Thailand. While some don't need a new one for either as long as you return to the same address.
First of all, give up on any idea of extending the DTV. It's almost impossible and even if you do manage to do it, you'll have to take so many trips to immigration and spend so much time in the attempt, that you won't even bother next time.
Just do a border bounce when you need more days. You're not required to spend any amount of time out of the country. You can cross a land border, turn around, and re-enter immediately for a new 180 day stamp. You can fly back same day if you can find a flight schedule that works.