We joined site unseen, but we had been visiting WDW for years. After a trip in which we had a bad experience with transportation and a bad room at a non-Disney timeshare, I came back, called
DVC for info and purchased. Also, the boys were at the age where they could go off on their own at Disney if we were staying on property.
After staying at many of the WDW properties, I debated whether I should add points to our SSR contract or buy a resale contract. I added points, but still might buy a resale. (I have not stayed at SSR for several visits, new resorts to try)
We have not run out of family members who want us to take them to "Disney," and have frequent inquires from local people who want to "rent" my points.
Depending on who is on the trip and the reason for the trip,different resorts work better for us. Also, now with a son in college, the ability to book 11 months in advance for our non-home resort is becoming an issue so I might buy a resale at a different resort so I can book 11 months in advance there. As the family changes and new resorts open, our needs and likes change, but we use all of our points every year and could use more. We have moved several times and it seems we meet our old friends, and old neighbors at WDW. We have a nephew who just recently graduated from college and is a pilot for a major airline. If he can get time off, he joins us for a few days at WDW when he can.
In addition, my hubby had a mild heart attack in his mid-forties, cause unknown. It was strongly suggested that he take regular vacations. He is now in his early 50's. He is not big on the parks, likes the Health Clubs, and just likes to relax in a nice room and read. It is pretty stress free for us to fly to Orlando, take Magic Express to the "World" and fly back. No rental car, we know what to expect in the room and no worries, and for a brief time, no snow. He sleeps, reads, works out and we can eat healthy in the room and in the restaurants. Just what the Dr. ordered. Since it is prepaid, we HAVE to go. No workaholic excuses for not going.
In short, works out great for us.