cd318:
I'm in agreement with your observations.
I rarely "listen to monitor" except when evaluating potential purchases I usually find upgrades very stressful although I've managed to make good choices. Having to re-establish system synergy after upgrading a component can be dicey but again, I've done allright.
I don't have the funds to regularly channel many thousands of dollars into audio, but the mere fact that I can afford modest upgrades every so often renders me suceptible to the very same syndrome you describe affecting the frustrated audio dealer. If one "listens to monitor" (or, said another way, pays more attention to sound than to what is being communicated by the music) one can easily miss out on the simple joy of listening for pleasure.
I find that after an upgrade,there's a "honeymoon period" during which I tend to spend more time listening, due to the novelty of "better SQ" and over time, as my ears become habituated to the improvements, I tend to listen somewhat less. Inevitably, the upgrade bug bites, and at that point, I have to decide whether to ignore it and deliberately focus more upon connecting with the music or give in to the desire for novelty, in terms of resuming the ongoing quest for "better sound".
I guess it's actually a blessing to not have too much money to spend on this hobby. Otherwise, I can see how one could spend all one's time chasing novelty, which would evaporate more and more quickly as one increased the frequency and cost of upgrades. One could end up like a hamster on a wheel, chasing something impossible to catch.
I guess what I'm suggesting is that it's a matter of mental discipline to manage the part of us that craves novelty and try to keep ourselves (mostly) focused upon that "child-like" pleasure, if in fact, that's one's top priority. I recognize it's not this way for everyone.