Classic cars in cold weather states...is it worth it?

Being from Alaska, you will want a 4x4 of somesort just because. I had many cars r wheel drive big and small in Anchorage with no issues. My mom still drives her PT Cruiser year round. Just keep it clean. They use more sand on the roads now anyway. You'll replace windsheilds often.
If you end up moving pm me and I can help between Tacoma and Anchorage to move cars, trucks and utility trailers.