Definitely get good about keeping air pressure.
One or two winters ago, I didn't get around to topping off the tires for fall. I usually tried to fill them to 42 psi after the temps got down in the 30's and 40's. But then one year I missed doing it and I landed and spun the tire on the rim because of low pressure, ripping the valve stem right off the tube half way. It rolled fine to the taxiway, but that was IT.
So my new policy is that I filled to 48 psi or so, in the fall when the temps were in the 30's. This way when I'm flying at 0F or -10F and the pressure drops even further, I'm not getting way too low. And, I will NEVER miss another fall tire pressure top-off. I do them every spring, too, but then I don't over fill at all because the temps will only get hotter.
And, I generally end up checking them mid-season once or twice.
Oh, and as others already said, make sure your gap around the tire is good enough. If not, it's a good way to rip the wheel fairing.