Thanks for you help. Now we just have to decide if it is worth it for us or if we are better off renting points / paying cash. We've been going to wdw once a year up until this year (wont be able to make it this year). The thing that worries me most is that there are always so many contracts up for resale...is that because it is a pain to try to manage planning, banking, and borrowing the points or do that many people just decide it's not for them? Also how difficult is it to get a reservation for the resort you want, is it much different than just booking a normal room?
Slappy and Mansion detailed why there are resales. As far as difficulty getting reservations, that is a question of many factors.
When do you want to go? Where do you want to stay? What type of room are you looking for? If you own at SSR (like we do), and you want to go to F&W, and you want to stay at BCV, and you want a 2 bedroom - well, you probably won't get it. Certain resorts fill up with owners at the 11 month mark depending on the time of year and the size of the resort. BCV and BWV during F&W are extremely hard to get unless you own there. On the other hand, we were easily able to get a 1 bedroom at BWV in March at the 7 month window. You also have to look at the points charts. The first 2 weeks of December are traditionally lower crowd levels, but they are also pretty much the lowest points needed to stay for DVC, so most resorts completely fill up. You can't always look at a slow time for WDW, since the points may be lower, and DVC members will flock to the parks then to maximize their points. You also have to look at the size of the DVC part of a resort. The VGF does not have as many rooms available as OKW and SSR, and it's on the monorail, so the rooms tend to book quickly during busy times of the year. You really need to be flexible and understand that you may not always get to stay where you want to. The maximum you can book is at the 11 month mark for your home resort, and 7 months for all others. Right now, I can book on the WDW website up until Dec. 31st 2016, so 14 months out.
Our strategy has always been to book our home resort right at the 11 month window to ensure that we have a room when we want to go. Then at the 7 month mark to the day, we call MS to see if we can change over to what we really want that trip. So far, we have gotten what we wanted every time, but we also tend to go at slower times. Of course, we haven't tried for BCV during F&W, but we will try for it at some other time of year on a different trip.
If you cannot plan a trip at least 7 months out, then DVC may not be for you. Unless it is a really slow time, booking at less than a few months out is next to impossible, though it can happen if you don't mind OKW or SSR as these fill up last. You might find a day or two here and there, but not a week long stay.
We are here to help, so ask any questions that you have!