I live on the north end of zone 5, i have no fig experience and recently picked up a hardy chicago fig on clearance and have it in a pot. I have no fig experience, in fact ive never even had a fresh one. I don't want it to get taller than maybe 6 foot or so at most if possible. Would i be able to get fruit set in maybe a 5ish gallon pot over the long haul or will i eventually have to go bigger? plan to root trim it annually.

You can get some fruit in that size container, but you will have to prune top and roots often after the first year or so. Welcome to the forum.

Fruit quantity is related to rootball (or pot) size. Smaller pot, smaller tree, less fruit. It is all a trade-off. See Bill's Figs Pot Presentation