We have been going to Disney most years since 1994 and bought last year when they built BLT. We liked staying at the CR due to its location to MK, our favorite park. The other DVC resorts didn't really interest us. Now that we have BLT and can still walk to MK, it made sense.
As far as financial, I looked at what it was costing me for my yearly trips and decided if I could own DVC and have 1 bedrooms instead of the hotel room at CR for no more than I was currently paying, it would be a good deal. My typical vacation for our family of 5 ran around $5000 per year so that was my target.
When I ran all the numbers, I realized that DVC would not cost me more, and in the long run, less so we went for it. Now that our family trips will most likely be 3 for a while (two are in college), the money I am saving each year is going to replenish what I took out to pay for DVC. Initially, we were going to finance but worked it by using the Disney Visa to get 6 months with 0% interest that was enough time to "pay cash".
Of course, we plan to visit WDW for years to come and are thrilled with our membership. The great thing is that you can get in to DVC with smaller contracts now, either by going resale or direct, and that may be enough to give you a feel for those EOY trips.
Basically, the way I figured it, I locked myself in to getting to go to Disney at a deluxe resort for at least a 30 - 40% discount. Prior to owning DVC, I kept hoping for a pin code to give me discounts (which never came). Now I don't have to worry about it. Plus, we have several family members who also love visiting Disney and figured there would never be a shortage of people to use up the points if for some reason we could not. Win-win for all!!!
Good luck!!!