I used my '02 Silverado 2500 with a car trailer to bring home the '42 about 170 miles one way. With my '59 Viking, I was planning to use a rented tow bar, because I thought that it would weigh too much for a standard car trailer. But I got lucky and was able to drive it all the way (65 miles) with only adding oil and coolant.
When I upgraded trucks a couple years ago, I went from a 1/2 ton to a 3/4 ton (glad that I did) as the difference in torque is like night and day.