In the past, this question had a pretty simple answer: go resale, unless you want your home resort to be one of the newer properties for which only Disney has points.
Nowadays, it's a more complex discussion. Yes, if you want your home resort, and its extra booking window, to be at one of the newer resorts, then the resale market isn't usually an option, and so you'll buy right from Disney. But these days, resale points come with some caveats.
You see, your DVC points can be used to rent more than just rooms at DVC resorts. Disney divides the options into a set of "collections," including the "Concierge Collection," the "Disney Collection," and the "Adventurer Collection." Points bought from someone other than DVC after March 2011, can't be used at any of those collections. Resale points are, primarily, only good at DVC resorts.
Now, whether or not this restriction matters to you depends a bit on what you want from your DVC membership. Many people buy into DVC to go to Walt Disney World and stay in the larger-than-a-hotel-room DVC properties. In that case, go resale - it's cheaper in some cases by 40% or so.
The "Concierge Collection" includes high-end hotels and timeshare properties outside Walt Disney World, and the "Adventurer Collection" includes vacations with Adventures by Disney. If none of that sounds appealing, then not being able to use them isn't a restriction. I'll point out, too, that using your DVC points on those locations doesn't always make good financial sense.
The "Disney Collection" creates the most argument amongst the DVC owners I know. This collection includes the non-DVC hotels at Walt Disney World, Disneyland, as well as the non-US Disneyland parks in Paris, Tokyo, and Hong Kong. I, for example, own contracts at BoardWalk and Old Key West - but I live just four hours from Disneyland. Disneyland's only DVC, at the Grand Californian, is pretty small and hard to book in the window I'm allotted, and so I tend to use my points to stay in normal hotel rooms at Disneyland Hotel or Grand Californian. This happens a lot in years when I can't get to Walt Disney World, giving me a quickie vacation at Disneyland with points I've already paid for. This doesn't mean I'm making a smart financial decision, though.
The financial value of these collections varies based on what kind of person you are. Take me as an example. Let's say I pay about $2,000 in maintenance fees for my points every year, and that, all told, they'll get me 11 nights at the Disneyland Hotel during the season I want to go. For me, that's a room rate of about $180/night - which isn't bad. I'm not necessarily getting a huge savings, but my goal wasn't all about savings. For me, it's about getting value from my points in years when I'm not using them to go to Walt Disney World, so "spending my maintenance fee" at Disneyland in a more-or-less break-even fashion works out.
Of course, I'm not factoring in the initial purchase cost of my points - but I'm OK with that. I'm also not factoring in the "opportunity cost," meaning the money I could get by renting my DVC points to someone else. In most cases, DVC members can make more renting their points than the value they'd get by using the points to book a hotel room. That is, my points would earn me enough to book my Disneyland hotel room in cash, with money left over. The thing is, I'm not going to rent my points. I find it a hassle that I just don't want to deal with, and it's a sketchy practice (technically not permitted by Disney) with which I just don't want to trouble myself.
But that illustrates the different sides of the "resale or direct" argument. With resale, you lose flexibility - that some would argue you don't need, and others would argue is financially nonsensical. Put next to the 30-40% savings resale offers, and that flexibility starts to look less financially attractive. For what it's worth, I bought resale pre-2011, meaning I got the best of both worlds - cheaper points and no restrictions. That said... I've never done anything with my points other than stay at Disneyland or Walt Disney World, so I barely use the flexibility I've got. We bought with the intent of going to Walt Disney World most years, and for the most part we've done so.
What will work for you?
Previously in the DVC FAQ:
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