There a tons of people living full time in harsh winter climates in all kinds of campers. Do a search and you will find all kinds of accounts of people using artic Fox and Nash campers for winter use with very few problems.
If you have electric hookups provided it will be very easy and cheap to use the camper in the winter as far as heating bills are concerned.
Towing would be the biggest issue in the winter, but beyond that it sounds like a good plan. Will it be a little work, yes.... but if you are in the same place for a week or more it would make sense.
The roommate and f150 will be your biggest problems.......25ft is the longest you'll be able to pull in a Northwood product.