I have a few years of use out of the PowerTank inflator set, and have the Milton one I picked up at the lws. I've noticed recently I prefer the PowerTank setup (with the qd, so you can use the double-ended, or a clip-on chuck).
http://powertank.com/products/sfID1/14/productID/146
The added benefit being you can push a button and let air out if you overshoot your target pressure as fast as you can put it in. The only time I don't use the PT setup is if I'm shooting ~300-400psi into a 19.5 to reseat the bead. Our 33' pusher had been sitting for a month, and somehow I didn't notice one of the inside duals went flat and unmounted itself.
Reached in with a clip-on chuck, shot ~40cfm @ 300psi in, sat the bead, put the valve core back in, clipped that inflator on, and finished it up. It makes tire maintenance easy enough you just walk around and do every vehicle you have at the same time.
I check the pressure and fill the tires on all my vehicles, family's vehicles, girlfriend's and her mom's car every Sunday. I had a bad blow out when I was much younger I attribute to having too high a pressure in the tire done by some garage monkeys. So needless to say, I check the tire pressures on everyone who's important to me vehicles once a week.
*edit*
Their digital version
http://powertank.com/products/sfID1/14/productID/368
I'm too rough on my equipment so I went with the analog gauge, but I've heard good things about their digital ones. You could always put a different brand digital gauge on it later.
The Wilton stays on my diesel truck with a large electric air compressor (5cfm@100psi, 20gallon tank) and the PT inflator stays on my mobile toolset, which usually lives in my fjz80 or who ever is going out of town, I lend a small setup to them just in case!