With a single hunting day of vacation (or two) and no opportunity to scout, your thinking about an outfitter is not a bad way to go for potentially greater success. If everytime we visited a WMA we saw and/or bagged hogs (we don't) I would say that recommendation would be better. When you get one on the ground, you will need someone to clean, cut, and ship it to you too. Also an outfitter does not guarrantee success either just a better opportunity IMO under these circumstances.
The Tossahatchee State Reserve is within 30 minutes of Disney and east alone the Beachline Highway. 28,000 acres of WMA with plenty of hogs, deer, turkey, squirrels, bobcat, racoons, armadillo, and other hunters. They may have a public opening hog hunt during your visit. Google the WMAs and see.