I think it's worth keeping a 20-30 gallon compressor in the garage with a long hose that can stretch out. They do a lot better going up to higher pressures and I don't personally like running my rear tires at 80 unless I'm towing so it's convenient to be able to air up for a trip and then drop it back down when I get back. Plus the trailer tires need to be topped off semi-regularly.
Nice setup. I haven't read through all of this thread but I think you are way below the point of stressing the truck at all even with the lift as long as your tires and wheels are up to it which I imagine is no issue.