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1) as often as it takes. The tire should always be at or above the factory spec.
2) this depends greatly on your tire, wheel, valvestem, and how well it was mounted. Some tires seem to hold air indefinitely, while some leak a few psi a month or more. You need to check your tires often to find out how they hold air.
3) 10F drop in temp will cause a drop of roughly 1 psi in a tire. I guess that's about 5 1/2 degrees C?
Low tire pressure can cause instability in the car, and can lead to tire failure at higher speeds and under load. It's much better to be a couple of pounds over the recommended pressure than to be a couple of pounds under it.
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