@Steven **********
you got limited options then, you'd have to show up on a 90 day Non-O, get 90 days, get a re-entry permit, get BACK in the country before that original 90 days ran out, apply for the year extension, get an under consideration stamp, get another re-entry permit, get BACK in the country before that under consideration ran out to get the year, THEN buy a multiple re-entry permit so you could travel the rest of the year
It'd take a LOT of coordination on your part to not run yourself off the rails time wise