Chaeng Wattana accepts bank letters up to 7 days old.
For other members, check with your local office for their policy. Some offices do the same as CW. Some accept a few days maximum. There are some offices that only accept letters on the day of issue.
Not true. As a rule, every single foreigner has to be submitted TM30.
usually, you need TM30 when you have to do something at Immigration office, not only "visa renewal" or extension application. Still the possibility you being checked by the police by chance is not zero.
If you mean applying for an initial in-country Non-O visa based on being over 50, no, no seasoning is required for that in Chiang Mai. You put the money in, get the bank letter would work.
Make sure you check the latest requirements of funds for an in-country Non-O in Chiang Mai. Some reports said no "international transfer" in requirements in Chiang Mai, some said you need to prove the funds were transferred internationally. I'm not sure the very latest requirements for that part.
, you can apply for 1-year extension based on the same reason of your Non-O visa entry. After that, you can apply for another 1-year extension every year as long as you meet the requirements.
Yes, visa-wise, IF your employer provides the necessary documents for him to apply for Non-O dependent on you.
But, it totally depends on the employer and your contract with them whether and when the employer would provide documents. You (or he) cannot apply for his visa on your own without paperwork from your employer.