OK thanks for the replies so far. Sounds like I'm not the only one who faces a challenge in doing this.
After my OP, I did some snooping on the Internet and found one on Amazon (see below) that I thought would work much better than my current approach. So I purchased one and it will be here Monday. I will post my thoughts after I give it a go.
I like that is has a built in pressure gauge.
Only $21.25 to my doorstep.
TireTek TXL-Pro Heavy Duty Tire Pressure Inflator Gauge with Lock On Chuck Free Bonus Quick-Connect air Hose Plug