Yes, sorry I was just verifying. Assuming you meet the requirements for a Non-O based on retirement, you can transition from a 30 day visa exempt entry to a 90 day Non-O. You'll need to have the 800k baht in a Thai bank account, but it doesn't need to be there for 60 days.
2 answers: Yes, you can get a Non-O visa while you're in Thailand.
-You cannot get a multiple entry Non-O, but you can buy a multiple re-entry permit after you've gotten the non-O, however unless you're leaving and coming back more than once after you get it, it wouldn't make much sense.