My only regret is not buying in sooner. I dismissed it out of hand for fear of the cost. Typically, I only have my daughter with me so that factors in to my pros and cons.
Pros:
*Staying at deluxe resorts that I never had before. Even with the wear on the oldest rooms, I still love them over the budget hotels where we used to stay.
*Having prepaid accommodations for decades.
*Enjoying the resorts without worrying that I'm wasting time that we could be in the parks because I know we're coming back. It really eases the stress of trying to fit everything in.
*Having, at the least, a kitchenette in the room. Full kitchens (rather, full-sized fridge) even better.
*Being able to use points at so many different places.
*DVC resorts are desirable so renting out points is fairly easy to do.
Cons:
*Annual dues come every year.
*DVC consumes my brain now like Gollum. Points, my points, I need more points. Gotta make spreadsheets for points. What's the latest DVC news on Disboards, FB,
YouTube??? J/K

...kind of.
* The costs of travel, food, and fun (park tickets, merch, etc) can add up if you don't budget well. Disney is expensive.
*Competing for room categories, especially when you aren't experienced with how quickly the highly sought after rooms can go or with walking reservations. I've haven't been in that competition so far, but I've heard the anxiety and frustration from others who post about it.