Thus spake bristle :
Okay, here's my take.
I check and retorque (as needed) about 500 miles after the tires have been off the car. Realistically you don't need to do that and, as you say, you don't have the skill set, nor, likely, the tools.
I do check my pressure once a week, as well as my oil. You should be competent enough to check the oil as it's written in the owner's manual and all of the rods are well (VERY WELL) marked. Air pressure? I've always hated the pop up gauges, but my in-laws gave me a digital instant read that's great. Accurate (it reads to the tenth, I'm only worried about halves) and repeatable.
When ever you walk up to your car in the open during the day, just walk around the car. You may not know what you're looking for right now, but in 3 or 4 months you'll know what's different, even if you don't know why.
You're whining that "that's something I can't do" is just that, a little whine. It's your responsibility to take care of your car. Unless you believe in the nanny state.