Here's my kit:
Compressor, dual foot straight pressure gauge, valve extender, 11/32's length of stiff rubber hose, and a big square knee pad:

I added short curved extenders for the outer dual, and added a small stiff wire brace to help with flexing. Dealing with the outer dual is as simple as a single tire:

For the inner dual, I have the standard rubber schrader values. I would have liked to had the metal style, but that's what's on it. Maybe next time when I get new tires, I'll get the metal valves, but these are servicable:

Using the short length of hose (3/8" may work better, this is what I have), reach in and press it over the cap:

Unscrew the cap, here's what you have: Easy cap control!

Then with the straight shaft gauge, reach in, center it and give it a firm press & hold to get the pressure:

If you need to add air use the extension. It's fairly stiff and the female end is fixed to the hose - it doesn't rotate independent of the crimp. Reach in, thread it on. You'll hear a little air escape, thread until it stops:

Here's what you end up with... the male end has it's own schrader valve:

Now attach your compressor and add the desired amount of air; mine has a threaded end. It's a little more difficult with a push on type - two people may be need. Thinking about this, a stiff extender about the length of the hose would be perfect:

It took me about 5 minutes to dig things out, setup and take pics. Checking and airing the tires is no longer a chore.
If no air is required, then all you need is the length of hose and gauge. I keep mine in my handy toolbox stored in the space under the fridge.