Let me tell you about our buying process. Perhaps that will give you the most helpful perspective.
DH & I decided that vacationing at WDW was something we truly enjoyed, and would probably always enjoy. We usually liked to stay at moderates or above, in terms of hotel and amenities, so in terms of cost per night, we were usually looking at at least $100/night, with an occasional truly great bargain of $79 or $89. It could also be as high as $250.
We looked into the DVC and determined a few things:
1. If you were going to go to WDW at least every other year, it was worthwhile.
2. It was a lot easier for us to come up with the monthly payment than the big "chunk of change" required for accomodations at WDW. It didn't seem like as big of a hit when it became part of our monthly budget.
3. We always be staying in accomodations that were at least the equivalent of a deluxe hotel room, and when you get into some of the bigger units, there is no comparison.
4. The location of the 2 (at the time-OKW & BWV) DVC properties was good.
We purchased in 1997. We bought 200 points at OKW, mainly because, at that time, the overall cost per point and dues were lower than the BWV. We also liked the size of the OKW units, although we love the location of the BW properties. We asked ourselves the question "If we could never stay anywhere again besides OKW, could we always be happy here?" The answer was yes, so we bought.
OKW is our home resort. We have an 11 month booking window there. We have a 7 month booking window everywhere else. We have never had a problem booking another resort at the 7 month window.
You buy points, not a block of time. You spend your points based on:
1.Time of year
2.Size of unit
3.Length of stay
Our initial purchase of points was enough for a 2 week stay in a studio size unit. We have, of course, since gone on to purchase more points.
Benefits of DVC (IMHO):
1. More space in your unit than a regular hotel room...more room to "spread out"
2. Washer/dryer in a 1bedroom or larger unit makes packing easier
3. Kitchenette(in a studio) or full kitchen (in 1 BR or larger units) can save you some $$ on food. We usually do breakfast in our room (it is just DH & I), but there are some folks with families who do breakfast and several dinners in their unit, which is a big savings!
4. Not having to come up with the big chunk of change all at once for the accomodations. As I said above, it seemed easier to me to make it part of our monthly budget.
5. I relax more about touring the parks because I know I will be coming back...I don't feel the need to "commando tour". This also enables me to experience some things at WDW that I might not otherwise experience, such as special tours, more time at the pool, renting watercraft, DH can golf etc.
DH & I are normal middle-class people. The DVC is part luxury, but we also consider it part smart spending, because we feel as if we bought 40 years of vacationing at a fairly reasonable price. It is some of the best money we have ever spent. We have never regretted it for a minute. We have taken family and friends with us and have had some wonderful vacations.