The first question I would ask my family is this:
"Do we want to own a timeshare?"
The difference between what you are doing now and timeshare ownership is huge. Right now, you are paying cash and taking advantage of whatever promotional opportunities make sense for your family -- in your case "Free"
DDP.
A timeshare is a very longterm, expensive financial committment... especially if you are talking about
DVC. With DVC, you will be committing to "Annual Dues" for the next 30-50 years depending on which resort(s) you own. And that is in addition to the substantial initial outlay to purchase DVC. In addition, timesharing requires more lead time in planning. You can't just call up and get a reservation 90 days from now -- you have to plan much farther ahead.
In order to answer that first key question, you should also take a look at alternatives.
Did you know, for example, that you can rent DVC accommodations from owners (rather than through Central Reservations)?
DVC rentals might be a better deal, and you can get DDP with those reservations as well. The DDP won't be "free," but your overall expense for a
DVC rental with paid DDP might well be less than what you are paying for your hotel room and "free DDP."
(In fact -- since you already have a reservation in place -- it might be a useful drill to research a rented DVC reservation on the DIS R/T board, paying for DDP and your park tickets, and see how the numbers work. If the DVC reservation is less expensive, you could cancel POR and try DVC -- which would be a twofer, less money and a test-drive of DVC.)
There are also hundreds of options OFFsite in the WDW area. Obviously you prefer onsite, but there are other options. Did you know that you can rent offsite timeshare 2 bedroom villas at very fine resorts for well under $1,000 for a full week? You can pay for a lot of theme park parking and meals with the savings from a deal like that -- and those options are commonplace.
IF you decide you want to own
some timeshare, the question then becomes
which one? If you want to vacation almost exclusively at WDW, and your family would not be happy staying offsite, DVC is an excellent choice.
But outside of WDW, DVC has only 4 other resorts (Aulani, VGC, VB, and HHI). In each of those locations, although the resorts are beautiful, most knowledgeable folks think there are better options than DVC.
Yes, you can use your DVC points in RCI, but DVC/RCI is very limited. You would only have access to <600 RCI resorts (out of 3,200+) and you would not be able to get FULL individual RCI membership, with the benefits that carries. Also, you should know that in ANYbody's timeshare system, anytime you exchange out to another system, you're almost always trading for a downgrade.
If you would be happy
offsite in comparable (or better) accommodations, or if you want to use the timeshare
for travel elsewhere, you should look at other systems. DVC is not the only quality timeshare system -- there are many, and most of them offer more options than DVC.
If you decide to buy DVC, my advice is
buy resale and
pay cash. Direct prices are DOUBLE resale prices in many cases, and financing adds enormously to your cost of ownership.