On the subject of financing - we financed and are happy with the choice to do it, but it took us a year of planning before we did it because if I did the math - this is what I got:
2005 vacation - close to 3,000 - Coronado Springs 7 days plus dining plan and no expiration MYW. I'd saved and we paid cash for everything - but would not have been able to save more than that per. year.
We had "done" Disney just about every year (I grew up in Florida and it literally feels like childhood and home to me), but this was the first time we had stayed in a moderate Disney resort and done dining and water parks for the whole week. I decided I could not ever do Disney without the luxuries of eating table service every night/staying at a meo/deluxe resort/having a week in the parks.
We attended a sales pitch and at the minimum buy in, over a year my payments would look like this:
1,500 - downpayment
approx 200 per month = 1,400
total = 2,900 - but not including 7 day tickets OR any dining (and DVC did not offer the
DDP yet). Even with annual passes and DDE, I knew I was looking at an additional 2,000 easily. So - even without the downpayment figured in - yearly cost of a vacation would be 3,400 (and the first year I'd spend 4,900!)
My issue at the time was that I could afford the club - but I would not have enough left over to buy tickets and meals each year.
Of course, in the long run - after the initial purchase was paid off, I'd be golden and loving the savings (one reason the extra 12 contract years really, really, really appeal to me). At the time, however, I was not sure I could comfortably afford to pay cash for the non-points portion of the vacations I wanted.
One thing the guides do not do, in my opinion, is prepare people realistically for the price of using DVC each year. I think this is the main reason people regret financing and/or their purchase of DVC.