How big of a tire could I fit on a factory Moab wheel?

Depends on how much lift ya have, my cousin runs 315/75/16 on her moabs. Not sure what size wheel spacers she has though but I know they’re there
 
How much lift do you have, and will you be running spacers? With a 4" lift you can fit a 285 on there comfortably, but at full lock (turning all the way to one side) it will rub, so you'd have to adjust the steering stops slightly.

For a 305 you're going to want a 1" spacer and 4-5" of lift.
 
I run a 315/75-16 and a 1.25” wheel spacer for an effective 3.75” backspace. Tires rub at full lock on the lower control arms. I run 3” of additional bumpstop to keep them out of the flares
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