The U.P.
Pretty cool place.
As far as skiing goes, the place to be is Houghton. Ripley has a sick park and get's deep. Fun little hill right by downtown. A good place to meet ski homies. Boho is only 45 minutes away and believe it or not there are actually some pretty accessible "backcountry" zones that are fun to hike out to in the middle of nowhere. Boho is awesome, and during the summer you have access to literally the best mtb trails in the state (arguably the best in all of the midwest) and all the hiking and public lands you can imagine. I've spent a decent chunk of time in Montana, and honestly, it's just like that, but with much smaller hills of course.
Houghton is also cheap af to live in. Even cheaper if you go north or south in the smaller towns. I pay 300 bucks for rent and I'm within walking distance of the waterfront and all the bars.
There aren't many people. Even when mtu is in session it still feels kinda empty. For some people, that's a positive thing. The Keweenaw is about is rugged and rural as it gets in the midwest excluding northern Minnesota. If you like the outdoors it's unlikely you will ever get bored. Also, you can ski, skate, and surf in the same day without driving for more than an hour. Lotta cool history and old abandoned mining shit up here as well. Also cool to bike downtown, grab a beer, and watch the seaplanes land on the portage.
I wouldn't go down by the Wisconsin border. You miss out on a lot of the cool shit that only the U.P. has to offer. Ironwood is just extended Wisconsin. So if you are going to make the move, Houghton or Marquette are the only areas you should go to.