There's a lot of wisdom in your post, tjkraz...for both us (
DVC members, Disney customers) and Disney...
At its heart, it's expectations.
What do we expect from Disney? And does Disney expect to deliver?
Pre-DVC, I experienced one trip w/out "Disney magic" at its beginning...and to this day I don't like that resort--I've been back, but it's always my last choice. And that less than wonderful experience kept me from returning to Disney for a couple of years. I chose different vacations during those years, when I could have gone to Disney but the "bad taste" of that trip caused me to prefer to go elsewhere...
Ultimately, I decided to try it again because the memories of "the wonderful" times at Disney were competing with the memories of that one "bad" trip (and it wasn't "bad"--it just wasn't "magical"--surly CMs, subprime service)...another BIG factor in deciding to try again was my DS...he hadn't been as put out (as a 12-year-old who didn't have to deal with any of the "issues") as I was and he wanted to return...and I wanted to please him.
The result was another "magical" trip (to a different resort)...and I "got over" (mostly) it...
But it illustrates my point. At the time, the "mega-money" (or so it seemed to me at the time) I was spending to go to Disney just wasn't worth it w/out "the magic." My willingness to spend the money rested on my expectations of "magic"--that sense that Disney gave me that there was nothing that was too good or too much trouble for them to do for me...once they treated me like "just another customer" I didn't want to spend so much money to go there...
My expectations are different now...DVC has changed things. First, there is an element of "being stuck with it" once the decision to buy is made (not that I regret it, but I can't as easily decide to just not go!)...and also I've now done enough trips that I more emotionally understand that there will be occasional "bad apples" or difficulties (and let me emphasize: I do not and never had held Disney to a standard of "perfection"...to me, it's more about how they fix a mistake (and their attitude about fixing a problem) than it is an expectation that everything will always be problem-free...)
So, where does that leave us (as a collective)? We can expect less, and perhaps be less willing to spend money on going to Disney (or buying into DVC). Or Disney can meet our expectations and thus ensure our desire to continue to spend money going to Disney (and/or buying into DVC).
The right answer is, no doubt, somewhere in between.
But it does all come down to expectations...