You cannot apply for a tourist visa inside of thailand. You will need to go to an embassy/consulate to do that. It would be better to start with that before you leave the US. As far as your whole family getting away with 2 tourist visas plus extensions and then exemption and extension is risky. You'd be better off getting a multiple entry tourist visa before leaving the US. It is good for 6 months and you get 60 days each time, and can get a 30 day extension each time as well. If you leave the country and reenter just before the visa expires you can get close to 9 months out of it.
It seems you, as many do, may be confusing two different dates. There is the visa validity date and the permission to stay date (entry stamp). The visa simply allows you to enter Thailand and as long as you enter before the expiration date you will be stamped in for whatever timeframe that visa grants. Or as in the OA visa it will be that or until your insurance expires, whichever is less.
yes, i understand things change which was why I stated that. I said it in the first place because many people just assume a tourist cannot, or ever could, without even checking. Others have also stated that some offices will give residency certificates to tourists.
yeah, I get that. Perhaps you are correct that most won't on a tourist visa. I can only talk about CM immigration, but I think it would be odd for any immigration office to require a 90 day report since it is not an actual requirement of ANY long term visa to stay in country that long. Plenty of people on multiple entry visas or other long term visas that leave for various reasons before a 90 day report is required. But then again this is Thailand and many of their requirements make no sense.
chiang mai will give one on a tourist visa, at least a few years ago they did. As far as needing 90 day report is only required if one stays in thailand for 90 consecutive days, which is not a long term visa requirement. I just got one and do not do 90 day reports becasue my multiple entry non-o only stamps me in for 90 days.
As long as you get married in Thailand before your last entry stamp expires on your visa then you can absolutely apply for the 3 month non-o visa based on marriage while in Thailand. You'll likely want to give yourself a couple of months after getting married to get all the paperwork and requirements gathered. Prior to the initial 3 months being up you then apply for the 1 year extension. Then repeat every year for as long as you want. It's exactly what I did a few years ago.
the two border bounce limit per year only applies to land entries. There is no limit to air entries, although practically the immigration officer may refuse entry if they feel you are abusing the system.