We own as well.
It works best if:
You stay in Deluxes anyway
You are committing to at least every other year at Disney for the next 40 years (or the next decade and sell - that's about the break even point).
You need to stay onsite
You avoid long weekends (weekend points at DVC are very expensive).
You can pay cash
You have a pretty stable financial situation
You want a multiple room unit (in which case your choices are DVC resorts, offsite, or the cabins at FW).
DVC does not work well if:
You are strapped for cash and
Disney vacations are a stretch - DVC pays for your room - but you need to pay dues every year, buy tickets, buy food, get to Disney. The initial buy in is nothing compared to the money you are committing to spend over the life of the contract.
You do a lot of long weekends.
You are happy offsite - there are lots of nice resorts offsite that are lots cheaper. There are nice timeshares in the Orlando area that can be bought for much less.
You are happy in Values - moderates are arguable - some people feel its a value over moderates.
You like "bargains" - DVCers can't get
free dining staying on points.
You expect a Deluxe hotel. DVC is Deluxe Hotel-Lite - mousekeeping is on a limited schedule for instance. I don't think the DVC rooms are kept up as well.
You absolutely need non-smoking. DVC does not (CRO doesn't either) guarentee non-smoking. DVC will not refund your points if you end up in a smoking room.
You are buying to trade out or cruise. The best value with DVC is to stay at DVC resorts. If you want to trade out or cruise occationally on those points, hey, they are your points, do what you want. But if you are buying for the purpose of trading out and are asking if I think that's wise financially, I don't think so.
You like last minute trips - DVC resorts work at pretty much fully occupancy - getting a room last minute is not always possible.
You need flexibility in cancellations - DVC is a timeshare with much different (and less flexible) cancellation policies than CRO.
You have a lot of variations in trip time and length year to year. DVC gives you a certain amount of points, and banking and borrowing can get you more points in any one year. But you need to average out over the life of the contract (or go through the hassle of renting out your points, or stay CRO, or do something else). For instance, if I want to go three weeks this year, I won't have enough points to go next year. Because of some strangeness in a family reunion trip and they way points worked out, I'm taking two trips six months apart (we are usually every other year people) - one I definately wouldn't be taking (and wouldn't have the airfare, etc) without having to "use" those points. A lot of people buy in their initial "Disney infatuation" and as that dies out (or their family changes) find they have too many points. Buy the minimum points to get in and buy additional needed points as add ons so you have flexibility in selling off as your travel style changes.
It can be more expensive and not save money. We go more often. We treat people to rooms. Because we don't have a room bill on checkout, we spend more when we are there.