All you need to provide regarding TM30 is the latest one (<- means with the check-in date later than any other of your TM30 records) with your address on the lease agreement.
Only the latest TM30 is valid. You don't need previous (or history of) TM30.
It does work, but only when you enter with both old and new passports. You show your re-entry permit on your old (invalidated) passport at the passport control at the entry point to Thailand, to get the correct entry stamp on your new passport.
Don't forget to transfer your stamps once you are back in Thailand.
You can apply for a 30-day extension for tourism purposes on or before the last day on your entry stamp. 30 days will be added (top-up) to your stamp, so you won't lose any day when you apply for an extension in advance.
, OP wouldn't apply for METV at all. He will apply for Non-O retirement in his country before he flies to Thailand, and enters on Non-O to be stamped for 90 days. He is planning to apply for a 1-year extension at the end of the 90-day entry stamp.
After into about three months on his 1-year extension based on retirement, he gets a re-entry permit to fly back to his country while keeping his 1-year extension valid.