I have had tires pop the beads very easily. I always clean the wheel and use a mounting lube. Getting enough air (flow) at once helps. I have a 10 gallon tank and it last a good while if things go right on mounting. For just topping off tires it last forever. If I find a leak I fix it.
The beginning of the year I had a pair of rear wheels that made popping the beads a task from hell. Almost nothing seemed like it helped. Just getting the tires on the wheel was really bad.