Buying DVC vs Renting points

I think the uncertainty would be a bigger reason to keep me out of resale. You may not care about Riviera now but might in five years. You may not think you will keep it for 20 years, but may find yourself in 20 years looking at your dissolving resale contract transfer options wishing you had bought direct when it wasn’t $300/pt.
Direct has more safety nets than resale for changing future needs.

But your personal situation impacts that calculation. If you’re 50 or 60 and buying DVC for yourself and grandkids, then your consideration for 20 years out is probably that you are less likely to care about trading resorts. But if you’re 20-40, then 20 years out May be more relevant. There’s no one size fits all in the math.
I think direct will have big benefits after the 2042 resorts expire. At that time not only will RIV be basically direct points only, but what ever other new WDW DVC resorts come on line between now and then. So after 2042 resale buyer will have a choice of the following resorts:
OKW (not sure how that will work with the extension but I'd assume still able to book there)
SSR
AKV
BLT
POLY
VGF
CCV

Still not bad options, but losing BCV,BRV,BWV takes a lot of rooms out of the system. It's one reason why we went ahead and bought 300 direct AUL points a while back and are selling our 175 SSR restricted resale points. That will still leave us with one resale contract, but it is a pre-restriction contract and should be good in the future.
 
Yep, in the end it’s good we have options. I see no issue with those that get resale or direct. Important thing is to just do your best to determine which avenue is best for you. Direct has more safety nets to changes, but will cost more in many cases (not all, when we bought resale would have cost equal to direct in the end, so it didn’t make sense).

I hope resale sticks Around as long as DVC does and we have a great market. I also wish Disney had never started the trading restrictions. I think it’s going to bite them in the long run if they keep restricting the resale market. I wouldn’t have bought into DVC if Riviera resale was actually as bad as some had feared it would be. But in 20 years when resale contracts work at half the resorts, if that, we may see a hit to resale value. That will keep more people out of direct or resale that aren’t absolutely sure they will keep it for 60 years.
 
I'm a teacher too, but it didn't work for me. For example:

When we started taking regular vacations with the kids, their winter break lined up with my "spring" break. We assumed that would be our "Disney week" for as long as we were interested in going. That lasted about three years before the weeks were uncoupled. So far, they've never been put back together (and both kids have been out of school for a while now).

When the kids reached HS age, they found that they really enjoyed and were committed to various activities---sports, band, etc. During those years, we went from taking 3-4 vacations per year to 1-2.

In the summer of '17, DW and I separated for several years. During that time, we didn't travel together at all.

Looking back on it, I guess I always knew when *I* could travel, but I never really knew who could (or would want to) come with me. And as our parents age and our kids establish their own lives (the youngest graduates from college this year) there will be even more unexpected twists and turns.

That doesn't mean one shouldn't give consideration to a UY. The one I would have picked at first would have been a good fit most of the time. But, my original plan of "always go to Disney in week 8" did not last more than about three years.

When we started, we chose June because all our family Disney trips had been summer, and from where we live, to fly for either February or April break was not feasible. So, that piece was easy. I also knew that when I retired, my plan would be to visit in the fall for F & W or the holidays, so June worked for those as well. Long range planning, that did leave March, April and May at the most risk which didn't seem like times we would go, now and in the future.

Of course, we ended up changing lots of things up, now have both Aug and Dec UY...those June UY contracts long gone...and we are set for all times of travel. But, as you say, things change for a lot of people and no one UY will work for everyone and every trip.

But, when it comes to renting vs owning, you have to be comfortable with the entire process and we never were. I do know there are plenty of people on these boards who have rented from the same person for years and in those cases, when you form a relationship, then renting may work out better because it doesn't lock you in the way owning does...but at least with a strong rental market at the moment, owners do have options.
 




















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