We have been contemplating this for 4 years now, and every time we are ready to bite the bullet, we back out. Why? I just don't think it's a good deal for us, and I have finally come to the conclusion that we are going to stop thinking about it, and enjoy our yearly stays at the regular resorts. Our reasoning?
Cost - No matter how I slice it, I cannot see it being a good deal. We stay yearly at either moderate or deluxe for anywhere from 8-10 days. With the deals Disney usually runs, dining, 4/3, 30-40% off a room, these trips average us 2-3K per year. That cost includes the room, parks and food. It's going to take a LOT of years to make that back, considering DVC is going to cost us roughly 16K up from, and 700-1K per year in dues, and that doesn't include park admission, or food! There is a reason Disney pushes DVC so hard, and it's not because it's a good deal for the "buyer".
The next big thing is not being able to take advantage of the deals Disney offers. i.e. the stuff I mention above that we take advantage of every year. We also LIKE the resorts. Being able to stay anywhere form CBR, to CSR, to the Wilderness or Animal Kingdom lodge is nice. Also, having daily maid service when paying these prices, and the option to stay at a monorail resort, is very nice as well. I admit, if I had money to just burn, BLT would be where I would stay, only due to location and the monorail.
Lastly, our kids are young. We really enjoy visiting Disney every year. But 10 years from now, when we finally "even out" our costs? Who knows, we may not be visiting yearly, or at all. As much as we love Disney, and trust me, I'm a fanatic, the kids already get a little bored after an extended stay. I would not want to dump a good portion of their college savings into DVC and wind up not using it 5-10 years down the road, and having to deal with selling it. (And who knows how possible any of that will be with today's economy and all that).
Anyway, I guess DVC is a good deal for those who really think it through, and are determined to use it to the fullest. I just think that for us, an average family that loves Disney, it's just not something I want to get into. I don't say this lightly, as I said, been looking into it for 4 years now. For us, we'll keep enjoying the "regular" resorts, and enjoying Disney all the same.