First, great deal with The North Face!
Second, my inflator actually has a threaded brass fitting that threads onto the valve stem. It's hard to see and kind of blends in. I too don't want to spend my time bending over and holding that thing on the stem.
Quick question, does you air gauge give a live reading when you're actually adding air so you can see the pressure rising? Or like most, do you have to stop a moment and let the gauge pressurize?
If so, I really like your setup and it's giving ideas! The only thing I would change is the digital readout. I really don't like tools that use batteries, especially tools that don't get used too often. It's just too easy to forget about them and then when you need it, the tool is flat-lined, dead battery. I'd much rather have a analog dial read out, and I always keep an LED head lamp in my door pocket which I check the batteries far more often that I would any other tools.
Also, and I don't know about your tire gauge, some of them use those dime size batteries, which makes it even more useless since you probably won't be able to cannibalize batteries from any other tool.
A little tip, I have ALL my equipment running on either AA or AAA batteries. I can always steal from one tool to use in another if batteries ever fail. This applies to all my Army equipment and regular outdoor gear.
That is one of the very few things I've ever found to be common in any country around the world (I've been to Australia, Africa, Central America, Europe, and most of the U.S. and I can ALWAYS find AA or AAA batteries!! Albeit, they may not be the best quality, but hey, they'll get the job done, right?