I'd say local, but then I went against my own rule already.
I'm in MI, I bet our hills are similar to WI. Local hills (4 nearby) are OK for park, but their season pass rates are upwards of $500 with no reciprocity.
The good hills are 4-hours drive away, so it's a mandatory overnight stay usually. I bought a season pass to Crystal Mountain MI for $229 on their early-bird sale. It pays for itself after 4 or 5 lift tickets, basically. I know I will use it at least that much. Look for early-bird pricing which might still be available often you can get season passes for 50% off the regular rate. I have seen them as low as $99 at some places which is absurd!
Locally I try to ride 1x a week at the resorts, I have used the Shell vouchers the last few years, at two of the local resorts these are good for buy-1/get-1 free lift tickets, Mon-Thurs. That means I can ride with a friend after work on Tuesday night for $16/person. Look around for deals like that. Get your kids to join the ski club. Volunteer to chaperone the ski club they usually give you free lift passes. Etc.
At the end of the day if you only have those two resorts to choose from I would probably get the local one and max your riding time. With a season pass, you can go any time even for only a few hours and you don't feel like you're wasting your money. Or if the conditions suck and you want to leave early, etc.