Unfortunately not in thailand they do discriminate with age for many jobs so they wont be too concerned about the older generation ( especially foreigners) using apps
I recently got my DTV from the London embassy and just showed one bank statement with the equivalent required funds in uk pounds , didn't need to show 3 months and was approved
The Visa or visa exempt crackdown. Has no impact at all on a non O visa, if you get a non O visa for your return you dont need onward travel at all since you have a long term visa. Don't worry either about the tdac you can put reason for visit as the most appropriate to you!!
The non O visa 90 day validity period is used up the moment you entered thailand and you got your 90 day stamp , you can't leave and return on that visa ans get another 90 days stamp as its used up/finished, other than what I have already said above about getting a re-entry permit.
You can get a re entry permit for your non O retirement visa before you leave to keep it valid But you will not get any additional time on your re entry stay you will only get stamped in for your original visa expiration date, so only a month left on your non O visa. The tdac it doesn't matter what you put as the reason for visit, holiday, thai family etc.
Thailand doesn't recognise common law marriage, you are either legally married or not. So if not married they wont see you as a dependent to would need your own visa if you are legally married then it depends on the retirement visa as Graham has already mentioned