It doesn't bother me that people ask for or get upgrades. I personally have never asked for one, it's just not my style.
But, I have to confess, in my past 9 trips, I've been upgraded 5 times. For what it's worth, I never go expecting an upgrade, and I always book the type of room I want.
I think Disney knows what they're doing when they hand out the free upgrades, and their strategy has worked on me (and my wallet)...
At AKL in 2003, I was upgraded from standard to pool view, so I booked pool view for my next AKL trip. When I arrived for that trip, I was upgraded to savanna. The next time I go to AKL, I will definitely book savanna view (totally worth the $$, in my mind). When I went to BC I was upgraded to water view, next time, I will book water view. In 2004, we were upgraded to woods view at the WL, with a view of the castle through the trees. I would probably book woods view in the future with hopes of the same view.
At the GF in 2005, I was upgraded to concierge, so what did I book for my upcoming trip to CR? You got it. Concierge.