Looking for recommendations

I have a couple similar to those. Holding them on the valve stem without air leaking is difficult.
10 Pieces Stainless Steel Dually Valve Stem Extension, Includes 4 Pieces Dual Tire Valve Extension 6 Pieces Valve Extender Adaptor for Most Cars Truck RV
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I got a Milton with a locking chuck for rubber tire loader tires for that reason takes too long to air them up, I do not love it because it cannot love me back but I sure to like it a lot.
 
That would be the cat's meow...was hoping to spend less than that though.
The one I showed you was $20 and work very well. My compressor goes to 115 lbs so I put it on the semi tires and walk away. It kicks in at 90 so if it gets to 100 lbs the compressor won't kick in and never overfill. For smaller tires you can install a regulator and set it where you want. For real lazy you can get a cordless compressor that has a digital display you can set whatever lbs you want and use the milton chuck that stays on and walk away. I think Milwaukee has one like that.
 
I'm looking for an easier way to air up the dual tires on my trucks and one trailer. I've got dual tire chucks, both straight and angled and holding them on there for the length of time to air up to 90 or 110 psi is a problem. Getting them to seal on the valve stem is also a problem.

I'm sure there are good systems and not so good systems out there. What are your recommendations for a way to more easily put air in them?
My problem is I have the valve stem extensions. There are no threads on the extensions. So none of my chucks will lock on there at all. And it does get old , holding it on there , if you are using a 125 psi air compressor.
 
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