Do what
@Steven *********
, suggested, Get a re-entry permit
You're on the last 90 day entry of your non-O , you're stamped in until the 5th of Nov. You're leaving BUT comin' back on on the 24th of Oct.
With a re-entry permit as long as you'd return BEFORE the 5th of Nov you'll be stamped in until that date. Then you can apply for your yearly extension of stay once you get back without having to start the whole process over