I also carry the Dewalt in my truck behind the back seat. I like that it can use a battery or a 12 volt cable. It has no issue inflating the tires to 57 psi which is what I keep the Oliver tires. When inflating tires it is actually my go to inflator rather than my big compressor.
I carry some 6x6 blocks which I have used to give me a stable base for the jack to sit on as well as an extra few inches height the two times I had to jack up the trailer on the side of the road (once for a flat tire and once when one of the drum brakes locked up).
When my children learned to drive I made them change a tire on the car by themselves. They had to pull out the jack and spare, jack up the car, remove the tire and put on the spare, lower the car back to the ground and then pull off the spare and put everything back where it came from. I just quietly sat in a chair while they worked.