Had one pilot at NJA I flew with that lived in a ski village in the Canadian Rockies. His wife was a photographer there. He drove 4-5 hours to Spokane, WA to catch his airline. He was in the program where you can cross the border fairly quickly.
Edit:
I've also heard of pilots who live in a RV and change bases every month or two. Usually their spouses drive the RV to the new base that they return from at the end of a trip. Great way to see the USA if you don't mind the nomadic lifestyle.