I know this is an old post but I'm new and wanted to share.
I bought into the DVC in 1999 with my Aunt D (one of 5 Aunts) she had been saying since the DVC started that she wanted to look into it. I was 22/23 at the time, had a full time job and on that vacation with her, my sister and her boyfriend I dragged her over to a kiosk on our last day. We talked with a very nice man, who's name escapes me, I used to remember it, and he sent us over to the Boardwalk to talk to someone. We got Randy Cook as our guide through the DVC.
Back then we went on a vacation every 9 months, so I left the math to my Aunt D and she quickly realized it would save us so much money in the long run, and we could stay at these awesome hotels. Normally we'd stay at the Value or Moderate resorts. After very little convincing the four of us decided it would be the best thing to do and my Aunt D and I bought 150 points that day! (Finally paid off December 2009!) I made her do it that day because we procrastinate and the paper work would have never gotten filled out. We weren't pressued or anything, in fact we were left alone in a conference room to discuss for quite a while.
A few years ago my Aunt D felt like buying more points, Saratoga Springs was up for sale and there was a deal with prices on points. At Christmas that year she spoke with my mother and the 5 other Aunts about the DVC and convinced all but 1 of the Aunts to join in. We bought 115 additonal points at Saratoga Springs. That gives us 265 points all together. You can borrow points from the next year and you can bank points from this year if you aren't going. Not sure how many ponts are available right now (it's a math thing we let my Aunt D deal with that aspect) but if we budget them right (OKW is the least amount of points for the week) we can go at least twice a year.
You can book at your "home" hotel (Mine being Boardwalk and Saratoga Springs) 12 months prior to your check in date...which I plan to do in April/May 2010 for my honeymoon in April/May 2011. I plan on staying at the Boardwalk in a 1 bedroom (love that tub!). Then I believe you can book at any other DVC hotel 6 months prior to your check in, I think we have decided before we were going to Disney in 3 months once and called the DVC and got a great room. All you have to do is make a list of your #1 hotel (mine Boardwalk) then choose a 2nd hotel, 3rd and so on, the people on the phone are wonderful! Their number is the easiest thing to remember 800-800-9800 the coordinators are so helpful and knowlegable. They will help you make all your reservations, room, bus to the hotel, dining, any special needs, the DVC is fantasic!