I htink if you go into it with realistic expectations, that you won't be disappointed.
DH & I have owned since 1997. We liked it so much, we bought a 2nd contract in 2002. Both are at Old Key West as our home resort. We have stayed in some of the other DVC resorts as well. I have always found them to be fairly well kept. They are not perfect, they do show some wear and tear at times, but when you think about the # of people who move in & out of them, you would expect mild wear and tear. IMHO, all I have ever experienced is mild wear & tear. I have also always had a very good response if I have called to have something repaired. It is generally repaired quickly and efficiently...there has always been a good response time. In general, my feeling is that Disney is not going to let their place go totally to pot. It seems to me as if they follow a renovation schedule, in an effort to keep things **** & span. I am also a propnent of reporting a problem when you find it, not 3 months later. The few times we have encountered a housekeeping or maintenance problem, we call right away. We don't wait until after we are home and then call, or worse yet, get home, post about it on the DIS, and never let DVC know there was a problem!!!!
In our mind, it is some of the best money we have ever spent. I enjoy having the ability to stay in a more condo-like environment. I enjoy having the extra space, the full kitchen and laundry(in a 1BR or larger unit).