While the Borg/Tireman extensions are the way to go for many folks, this has been my method for a decade:
Kit:

Small metal extensions - tighten the inner fitting with small pliers. I've never had a leak with these on both our Ford (shown) and our current Sunseeker based on the Chevrolet 4500:

Leave the inner dual as is - no need to add an extension:

Using the short piece of hose, remove the inner valve cap:

Result:

Check the pressure with the double footed gauge:

If it needs air, temporarily use an extender. The female end fitting is fixed; it does not spin on the hose, so it can be spun on using the hose:

Result:

Attach your compressor, and add air as needed:

BTW, I'm one of those 5% who DO rotate tires! I don't remove all of them - I just lift the desired axles, but I did remove all when Michelin had a recall a few years back:
