I have a compresser, but I only use it as an inflater for car tires. It takes longer to pull it out, plug it in and wait for it to come up to pressure than to grab the floor pump and do it by hand for bike tires. The compresser also makes a racket.
Regarding wheel bearings, IMHO cup and cone are superior in almost every way to cartridge bearing for this application. They will last forever if properly maintained, you don't need special tools to change them (well, a cone wrench) if not properly maintained, and by their design they handle lateral loads better. I had a set of Mavic wheels, now have Shimano, and would not go back.