I can go on Booking.com right now and find 50 options for Key West. Then go on Airbnb and find another 100 options for Key West. Why am I buying a timeshare?
I have an anecdotal answer. Our first several years of annual WDW trips were booked via VRBO. We would get a townhome or pool home, usually at Windsor Hills, within spitting distance of the parks for a really good rate. And, when I say "spitting distance" I mean: I could put the Wishes CD in the player when I started the car in the MK parking lot, and be parked at "home" and have the car turned off before it was done. The entire CD is just over 15 minutes long. When I say "really good rate" I mean: the home rental plus rental car and theme park parking usually came in somewhere between a single Value room and a single Moderate for the same dates.
But, scouring VRBO is a royal PITA. All of the homes are different. Some are pretty obviously well-kept, others are...not. But you have to actually look at the listing to figure that out. The prices vary widely, and they mostly but do not always track with the quality of the interior. Throw in the "there might be something better" FOMO, and it was a non-trivial undertaking each year to find the right place.
Plus, VRBO (and Airbnb) properties are not resorts. It's like staying in your fairly well-to-do Uncle Doug's vacation home while he isn't using it himself---and that was literally true one year! They are very nice, but the vibe is totally different from a resort, even at a short-term rental community like Windsor Hills. When the kids were little, this was perfect--we wanted the quiet and more private vibe of a rental home. But as they grew, we realized we wanted to stay somewhere with a bit more "vacation energy."
Those two factors led me to consider a timeshare. I ended up passing on
DVC, becuase (a) doing that for our annual Disney trip would have consumed our entire vacation budget and (b) I was worried about the kids "aging out" of Disney before I reached the payoff horizon. Instead, I ended up buying a resale Wyndham timeshare for about a dime on the dollar, thinking I would use it for Bonnet Creek every year. It wasn't any less expensive than just renting as I went---even as an el-cheapo resale acquisition---but it was a better solution to our Orlando vacation needs. It also turned out to support a LOT of other really fantastic vacations I would never have taken otherwise.
So, TL;DR: A timesahre gave me a recurring, consistent resort experience for a very good price with minimal ongoing work to secure it.
resale RIV (for the right price) is the best play in
DVC.
I'm starting to think that might be true. I would never have considered it if I had not already had direct RIV points, but there is surprising value there for folks who would like to stay at RIV regularly.
overvalues the ability to exchange into other resorts
I'm not sure that's objectively true, becuase this is necessarily a subjective value. Some people might place a huge value on novelty. Others would be perfectly happy to do the same thing over and over. I don't think there is only one answer to this. I do suspect that people
think it will matter more to them then it actually
would, but perception, reality, blah blah blah.
I do think there is one subtlety that is worth adding to this. If one is primairly interested in studios, the ability to exchnage narrows pretty quickly. So even though you can do it
in principle, in
practice it is a little bit harder. However, if you are a 1BR person, then the world is much more your oyster.
undervalues length of contract.
On this, we agree.
Looking at an example for Riviera staying 6/7/26 - 6/14/26
I appreciated this! But I also do think it is worth considering that Dues are not the only cost. Worse, in the earlier days of ownership, they might not even be the dominant cost.
Everyone does this a little differently, but when I want to know the "cost" of one of my DVC points, there are two factors. The Dues, and the apportioned cost of the per-point purchase price for that year's point. I'm a dork, so I don't use straight division for this. Instead, I amortize the purchase price across the life of the contract at some reasonable esimate of inflation. (I tend to use 4% as a conservative estimate of the long-run US inflation rate.) When I do that, I'd come out at a slight loss on my developer points vs. the 40% passholder promo in either 1BR, but would pretty much break even on the 30% version.
Happily, the resale points remain in the black no matter what. Furthermore, over time both should improve vs. prevailing rental rates. that's becuase only Dues are subject to inflation, while the amortized purchase cost is in constant dollars. That won't be true for rental rates. This is the same line of thinking I use when I explain to my kids why it is sometimes worth stretching to buy a house vs. renting. The only inflationary terms as a homeowner are taxes and insurance; principal and interest stay constant.
Of course, that ignores maintenance, which is also inflationary, but seeing as I just bought a 90+ year old house, I'm not going to think about that very much!