Disclaimer: Please do not let my experiences influence what you expect!!!
We don't usually ask for anything special. My DH is super lucky, and we've gotten several very awesome upgrades. People just give him things
We were upgraded from Garden view Poly to Concierge Poly for 9 days.
We were upgraded from Standard room to Water view concierge at Yacht Club.
We were upgraded from standard Boardwalk Concierge to Boardwalk View Concierge.
I've also been upgraded from standard to water view at POFQ on my own, as well as WL, we had couryard view booked, and I was upgraded to concierge. At POFQ I asked, willing to pay for it, I had been trying to change categories for a week and nothing was available so I asked at check in and they just gave it to me. WL just informed me I had been upgraded. Such a great surprise! So I guess I'm a little lucky too.
I've usally gotten my room requests as well...pure luck. I don't go in expecting anything! But, I've gotten the building I requested at POR, the building I requested at Pop, the savannah I wanted at AKL and the floor, and when we were upgraded at WL I still got the same view I had requested. Awesome!
Funny thing...now I usually book concierge because we love it so much...so Disney was smart about giving us upgrades. We now have a Garden view concierge booked at Poly (fingers crossed, maybe we'll get lagoon). And in November, we are staying at the ultra super expensive 14th floor Contemporary. Believe me, Disney is cashing in on the upgrades they've given us!