The match in both directions seems to work most reliably after any old status has expired, so yeah I would say wait until after Oct 1 (by which I mean like Oct 5, because Mlife is not the most on-the-ball at updating their systems) and then rematch into Mlife if necessary.
Mlife seems desperate for more elite members with all of the promotions they've been running so it's possible they'll extend your status even if you haven't earned it; they did that for me the last 2 years. I'm guessing if you've done some business with them, even if not a lot, it helps the case for that treatment.
Then you have Oct-Feb to make sure you match into Mlife, and then Mar-Sep to make sure you match back into Hyatt.
