You will find that many on these boards will preach the adage of "no debt at any cost", but in reality it's all about balance and what you feel comfortable. For me it is mostly about liquidity.
For example, in this thread it has been suggested that you should not buy a luxury purchase if you have a car loan, well if you purchase your car brand new and you have outstanding credit, it is likely that you are paying little to no interest anyway. Why should you be in a hurry to pay off your car loan, and use up your cash, if it is not costing you anything?
That being said, part of being a responsible consumer is really knowing what you can and cannot afford regardless of what a sales person tells you. Sales people probably love and hate DW and I. For one thing, with major purchases we generally know whether or not we are going to buy before we even talk to a sales person, so they really don't have to convince us. On the other hand, we generally do not make good targets for sales people because the "pitch" generally does not work on us, because I refuse to make major purchases without taking the time to do the research. For example, we never talked to a DVC "guide" prior to purchasing. My brother was a DVC member and we stayed on his points one year. After that, I knew I wanted to purchase, so we contacted our guide and told him how many points we wanted and at what resort.
Many people are on edge since 2008 because of the state of the economy. Many who never expected to be out of work, suddenly found themselves out of work. However, some careers and jobs and locations are safer than others. Only you know how safe you feel with your career (not necessarily your current job) and what your contingency plan is.
As for DVC, we financed and it worked out well for us because we were able to buy into the resort we wanted (BLT) while we could still afford it. If we had waited until we had enough saved, we probably would not have bought at that resort or would have had to purchase fewer points.
As others have said, it all comes down to risk and how much are you are willing to risk for your vacations? In our case, I am willing to risk quite a bit because looking forward to vacations is what keeps me sane
If my choice was complete financial stability without vacations or having a manageable amount of debt with my annual or semi-annual vacations, I'll take the later. The "trick" is knowing what is "manageable".
I was beginning to think I was the scum of the earth just for having a car payment. I will reiterate: I don't have ANY credit card debt, or student loans. (My and my husbands student loans have been paid off for years.) We deposit into our savings accounts substantially every month so that we do have that "cushion" that we all should have. We invest in our retirement funds, and our daughters college fund soundly. I do have an investment portfolio. In all of the years I've been traveling to Disney (As a child since 1974, as an adult paying my own way since 1990. The year I graduated high school.), I've not ever once used a credit card to pay for my trips or used one while on vacation. I just figured that maybe DVC would be a smart decision for us as I will continue to go every year and sometimes multiple times in the same year. We usually stay Deluxe for an average trip length of 10 days. I thought DVC will save me money in the long run as once again I already have the financial means to take multiple trips a year without going into debt or stressing my finances in any way. I simply was wondering what kind of DVC advice the DVC experts would share with me. Sorry if this comes across as argumentative, I just never thought I'd feel the need to defend my financial security. Still love the DIS though!
Thanks so much to those who did offer their suggestions on what has worked for their families. It has helped me in my decision. I think I will take your advice and buy a small resale contract and add onto it every so often until I have the number of points our family will be comfortable with. Now the fun starts! 
