I have figured out the upgrade itch

My rules for the upgrade itch:
1. Keep the damn audio mags in a room away from your system. Reading them while listening ensures component buying fever.

2. Ditto for the laptop ;)

I find that critical listening to components is stressful and I will now be doing my best to avoid it. Critical listening to music is an effort for me because I am not musically trained; as in Art, I don't know what's good but I know what I like! So I now want to listen for fun.
All the posts above have some good stuff in them. Yes, the glossies inspire lust, not unlike Mr Hefner's brainchild. Tantalizing angles in photos, soaring hyperbole, new version comparisons inevitably trashing the old and lauding the new, and the esoteric and often painful vocabulary employed, all conspire to force one to spend money for the benfit of advertisers and the mags themselves. At least Hugh H. does not run a brothel (to my knowledge), but his work (and that of his better imitators) does raise the bar for judging women's beauty.
One needs to be reminded that many of these audio critics are in smallish apartments in NYC or London and many times don't have the environment to make a given component perform to full potential. Then there is the issue of memory. Being of at least average intelligence (but don't ask my wife!), I have a hard enough time comparing two CDPs if I heard one of them only yesterday. And these guys dig months into their memories!
Many hobbies have the potential to degrade into obsessions, and this is certainly one of them.
Teetering on the brink of insanity...

I think the glossy rags lead to my upgrade itch. They wax on and on lyrically about what a tremendous improvement the mk II version is over the mk I, that I start listening more critically, and finding more 'problems' with my own system. I find it best to cancel my subscriptions, and just listen for fun. Even really bad recordings where I like the music are suddenly tolerable.

I agree with you to a point - you seem to distinguish between critical listening for the sound of the components and "serious" listening which includes listening to music while doing other things, such as reading. How about introducing a third type of listening, that is, critically listening to musical content. Then when you get the urge to upgrade you just go out and by some unfamilar music to satisfy your need to listen critically. There is just so much music out there to be discovered and enjoyed. Why waste your time worrying about how different components sound. :-)

I've come to believe that "serious listening" should be seen as an oxymoron. That's probably not exactly the right word, but why is what is supposed to be a hobby and for pleasure ever "serious"?

Which is another way of saying I agree with you, although possibly one symptom removed. It's when you stop listening for enjoyment, which doesn't necessarily mean listening while doing something else - you can listen for enjoyment in a dedicated way, that you start analyzing the sound. The activity you're doing has changed its nature, quite possibly without you overtly deciding to do so. That's not the sole reason a person gets the upgrade itch, but it certainly is a leading reason.

Well Hughes12 I listen to music for enjoyment.
Sure we listen critically when we upgrade but after a while hopefully we just relax and enjoy the music.
I would say "serious" listening takes up 80% of my time spent-it drives the girlfriend nuts.