I've got a 5 gallon air tank and a little "shoe box" Black & Decker air pump. It suits my needs. I usually pump up the tank to around 60 psi, the little compressor struggles a bit beyond that pressure.
I can generally top up the tires on 3 cars in the driveway with the fall seasonal air pressure drop, generally 3 to 5 psi per tire, before recharging the air tank. I'll give the air tank a full charge before topping up the spare tires, spring and fall.
Sometimes I'll use the set-up with a blow-off gun for little jobs like blowing out spark plug cavities before removing the spark plug. The blow-off gun works OK for small jobs.
The tank's not too bad to lug around the cars. I don't have a heated garage (you get water in the bottom of shop sized compressor tanks) and I never felt the need for a full sized compressor. The small tank never seems to accumulate water. I've turned it over and vented it, but no water comes out.
For filling a tire out on the road in an emergency situation, I'd consider one of those small 12v air pumps. A dinky air pump will get the job done, it just takes time, maybe 10 or 15 minutes. I've got one of those in the trunk of my car.
Just my experience.