Get your TM30 from your landlord then around the 90th day of your DTV stay you go to Immigration with your passport and TM30 for your 90 day report (complete a TM47 form). It is free.
Why did you get problems with a 30 day extension? When you get your entry stamp the 30 day extension is virtually a given, very unusual even to be questioned.
Your plan will work with your onward ticket and you should have no Immigration issues unless you have a recent history of Visa Exempt entries especially if you took the 30 day extension.
Is your Non-OA Visa expiring or is your 12 month permission to stay stamp in your passport expiring. If it is your Non-OA and you have insurance for 12 months you can do a border bounce to get a new 12 month entry stamp. If you extend in country you need to go to your Immigration Office and get their list of requirements for your particular visa type.
Do yourself a favour and leave then re-enter and apply for a Non-O retirement visa which still has the same financial requirements as a Non-OA but no insurance requirements so you choose insurance to suit your needs not theirs.