I hate extra work, with 60+ tires on the ground, my solution is to invest in
tire plugs
valve stems
Schroeder valves
long handle 4way lug wrenches
extra rims with mounted tires of each size needed
extra free takeoff tires from friends
standardize as much as possible on rim sizes
multiple heavy duty hydraulic long throw jacks, bottle jacks with wood blocks, tractor jack
12v air pump(last resort)
air compressor, large capacity, with high torque impact wrench and sockets
multiple tire gauges
visually inspect tires every time I use a vehicle/trailer.
HFT tire changer but most often take tires to be mounted to excellent local tire place
patience is greatly facilitated by knowing all the above are available for resolving a low air problem.
being retired helps with perspective on the problem.
Dry rot always gets my trailer tires. I've never came close to wearing the tread off of a tire. Once I start to see cracks forming they get replaced the next time I need the trailer. For around the house I'll use tubes. I wonder what would happen if you pulled the wheels and put them in a shed or garage until needed, maybe even at a reduced pressure for those of us that rarely use the trailer.