I've never spent enough time in really cold climates to have to worry about this. But it seems to me that what matters is the pressure in the tire after it gets warmed up. My (admittedly naive) intuition says that a tire will get almost as hot driving on cold freeway as on a hot one. Doesn't most of the heat come from the flexing of the tire rather than the ambient? If so, your tires will be seriously overinflated when driving if you blow them up to the sticker pressure when they're really cold. Maybe driving slowly on a snowy road wouldn't heat the tires so much. But don't you want them a bit under-inflated in that case anyway?
No, No, No, No, No!
!. Heat, not pressure, kills tires. I don't know where people get the idea that putting some air in the tires is harmful--it's not. Well, fifty years ago, when we used bias-ply tires, if you put too much pressure in relative to the load, the centre of the tread would wear out quickly. Radial tires typically don't have this problem because most have a very large crown radius and the belts stabilize the tread. For almost all on-road use, you never want the pressure to be less than the vehicle placard pressure. If the day is hot you want it to be higher. If the day is cold and you inflate with indoor air you also want more pressure to compensate.
2. If you put 25 psi in one tire and 45 in another and drive for a couple of hours at highway speeds, both tires will have about the same pressure due to thermal equilibrium. However, the tire starting at 25 psi will be far hotter and may even debond. At the very least the compounds in the tire will have been substantially degraded.
3. The maximum pressure on the sidewall is for cold inflation first thing in the morning. It's not a problem (and in fact is perfectly normal) for the tire to have higher pressure after driving. Ideally the pressure increase is under 10% if the day remains relatively the same temperature, or 15% if the day grows significantly warmer. If it increases by 25% you need to find out what the cause is.
4. You never want to adjust pressure in a warm/hot tire. (This doesn't mean not adding air to a leaky tire to get to the repair shop.)
5. All tire pressure recommendations are based on a set of assumptions. One of them is that the ambient temperature is 18 C (65 F), another is that the pressure check is done cold, first thing in the morning, on every driving day. Change the assumptions and you need to change the pressure. The change is almost always upwards.