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I have those cheater caps that turn red when the pressure drops under 30psi. i always give them a peek when i go by. As far as using gauge i dont do that unless 1 is in the red, then i check all 4.
You could tell when one tire looks lower than the other ones. Most of the time, a good quality tire will hold the same pressure for at least 3-6 months or possibly more. Temperature will cause it to contract & expand, so there is a little variance whenever you have a temperature (climate) swing or a road trip. On an average, most people add a few pounds to it about once or twice a year. The other option is to get an aftermarket TPMS system to monitor it everytime you drive. Al, did you look into using nitrogen instead of regular compressed air?
I check every three months or so or just before I set off on a long trip. Last time I checked all 4 were at 26psi so I pushed them up to 33psi. I'm good to go for another few months now.
I visually inspect my tires every time I get in or out of my truck. There's always some kind of construction work going on around where I live and it's real easy to pick up a stray nail or screw or other piece of pointy metal with the tires. I check the belts, coolant, ATF and oil level about once a month. T-case and differential gets checked 3-4 times a year, start of spring, start of/end of summer and start of winter.