I have a set of raidials that are square from sitting, but they sat longer than one winter. If you're going to let the car sit all winter, it doesn't involve that much work to put the car on stands. On stands, you want to keep the springs loaded meaning that you support the car under the control arms and under the rear.
Now that I have square tires on steel rims, they have become the car's winter sneakers. If I want to take the car out and poke around, I can run it around on the winter sneakers because the square factor doesn't come into play until about 50. The poke factor would be speeds from creep to 35 to 40, and if I had a burning desire to go faster, I would install summer sneakers. I guess it depends on which side of the tracks you come from, but I view the r&r of 4 tires--twice--as about the same amount of work as adding a quart of oil.