I've stayed at all of the above!
Contemporary or one of the other deluxes
Shades of Green
I stayed at the Contemporary as part of the Shades of Green rehab. The location was fantastic. We could walk to the MK. We could monorail to Epcot. We could watch the MK fireworks from the parking lot and the boat parade from our room. The room was very spacious and comfortable.
Old Key West or another home away from home
We're members at OKW and BWV. I have also stayed at VWL. All are great for their own reasons. The main advantages of a "home away from home" is the extra room and the cooking areas. In a studio you get your own microwave and refrigerator. In a 1 BR you get a full kitchen and your own laundry facilities. Ah! Heaven!
The Allstars
I've stayed at All Star Music and All Star Sports. I liked Sports better, but I am a huge baseball fan. The rooms are small, but the themeing starts to grow on you after a while. The food courts are fantastic and the bus system is the best on Disney property.
The Moderates
CBR is my only moderate. I was very lucky to be near the OPR, otherwise it would be quite a walk to the food court. The room was comfortable and the resort grounds were very relaxing. I loved the islands theme. The bus system was great at CBR too.
Downtown Disney Hotels
I've stayed at the DD Hilton with my husband on business. It was OK, but dull. It had a great location to DD, though and the double decker hot tup was very cool (yet, hot

. I also stayed at the Wyndham Palace on Priceline. We had a great view of Disney and Universal fireworks from our balcony.
Swan/Dolphin
I stayed at the Swan last December via Priceline and it was fab! The room was very comfortable and it had location, location, location. We were upgraded to a room with a balcony where we could watch the Epcot/MGM boats come in.
Offsite
I have stayed off-site lots. I use Priceline and stay off-site to save money. We have APs and always rent a car so staying off-site stretches our Disney vacation without too much of a hassle. I've stayed at the Marriott Orlando World Center, the Rennaisance Worldgate, the Wyndham Orlando and many others.
Timeshares
I did this once because I got a great deal I could not pass up. I stayed at a SunTerra resort, Cypress Pointe for $150 for 3 nights in a 3 bedroom condo with a rental car. Of course, we had to give up 90 minutes of our time too. Since we own at DVC it was easy for us to say "no" and for them to accept our answer. It was better than your average off-site hotel and the sales pitch was not so bad either.