In some cases neither of the trucker style chucks will work. We have 22.5" wheels on our 2013 Winnebago Adventurer. I have both style chucks on Milton inflators. Neither would fit through the small hole in the outer aluminum wheel and align with the valve stem on the inner wheel.
Rather than add valve stem extenders I modified one of the inflators. I used the one with the angled foot. I removed the original 1/8" pipe extension between the gauge and the foot and replaced it with a 12" length of 5/16" brake line and an adaptor on each end. I bent the brake line to go through the outer wheel and allow the foot to connect with the inner valve stem.
The inflator I use looks like this, but has an angled foot rather than the straight on one.
http://www.northerntool.com/shop/tools/product_48541_48541
The foot on the chuck looks like this:
http://www.northerntool.com/shop/tools/product_42493_42493
Keep in mind I only used the foot, not the complete assembly. I got the brake line and adaptors at our local NAPA store