I agree that sometimes one has to use the brake a lot when micro-maneuvering into relatively tight spots, especially backing. But 10 to 15 times in a couple of minutes is quite a few. That said, I would expect the engine's compressor to kick in before the low pressure alarm sounds off, which on my Monterey is in the neighborhood of 65 psi I think.
Although I agree Dick's repeated tapping of the pedal is the cause of the system pressure loss, the fact that it isn't recovering better is bothersome regardless. I think the parameters for the compressor are cut-in at around 105 psi and cut-out between 120 and 135 psi, 120 is more common. I presume he's flipping the switch to high idle when parked and trying to recover pressure with his foot off the pedal, parking brake applied. It shouldn't take that long to get from 105 to 120. And if the compressor cuts in at 105 while maneuvering, it should at least counter his braking and not let things fall clear down to the alarm level. Might he need his air governor checked just in case repetitive braking isn't the only causative agent?
Dick, have you or BCS purged the air tanks lately? You know, completely drained the dry and wet sides of each via the gang of 4 brass petcocks? If any moisture is noted when that is done, I'd consider whether the air dryer/dessicant cartridge needs attention, although I'm not savvy enough to say a problem there would actually slow your progress to 120 psi.
Joel