i also have shop air and had the same problem. plus, i just didn't like those finicky little presta valves. so i drilled out the rims on my 'bent bike and went to schrader valves. eventually i had to buy a decent floor pump with gauge for a trip. now wish i'd done this in the first place. i can now fill my tires before my compressor can build enough pressure. i too for some reason like the sound of the escaping air when i release the pump chuck.

OP here. I'm done. Rims were double-walled. Inner hole was bigger, I just had to drill outer rim, used 8.5mm drill bit. New tubes in, we rode that bike for some miles and all is well. I'm happy.

I guess I have 2 new tubes for sale on craigs list :)

That's what I think too. If you have a shop air compressor, you can inflate a schrader valve tire in about the amount of time it takes to "burp" a presta valve.

In the interest of full disclosure, all of the bikes currently at our house happen to have presta valves but facts are facts.