This set up belongs to one of the members on this forum. I can't speak for the "comfort" of driving, or if it is a good idea. I have towed some crazy stuff over the years. (some of it I probably shouldn't have)
We tow a pop up behind my 6cyl Ford explorer. I have towed behind a 6cyl Dodge Caravan, and have towed behind a 4cyl Jeep Wrangler. The Jeep was the most challenging and I would not take it very far. The others I took well over 100 miles.
As for year round camping, A pop up could get cold. A teardrop camper will tow very well, but again for year round camping probably not the best choice.
