CCV went on sale in March 2017 for $176/point, and again that's with no incentives. Depending on the price point someone bought into, chances are they are breaking even if they are selling now, because they probably got it for around $145-$160/point -- not to mention having gotten 3-4 years of use.
DVC Doctor's suggestion of 75% seems spot on.
While certainly none of us know what the future will bring, I think history has shown that if you hold your contract for 10-15 years, you will likely break even when you sell if you purchase direct (except perhaps if you are purchasing 2042 expiration resorts, since in 10-15 years they will only have 6-11 years left). And while we certainly don't know what RIV resale will be like in the future, it's current resale value is holding up remarkably well against expectations.
This thread is getting pretty complex with lots of math and opinions throw around, so let me clarify my opinion as a 20 YEAR DVC Member that has seen lots of ups and downs.
My first rule #1 is to pay cash for a new or resale contract and do not finance with 10%+ interest. If you want to use a HELOC or some other low interest rate (under 5%) then that is acceptable. However, if you are financing at above 5% then I would advise NOT TO BUY and just rent points or pay Disney cash rates. I do understand that that may mean a large outlay of cash and not everyone has $30,000 laying around, but that is still my #1 rule as the money wasted on financing far outweigh any potential savings you may be planning.
The DISboard common rule #1 is to buy where you want to stay has not proven true for me as I constantly jump resorts and NEVER use the 11 month booking window. If you need the 11 month booking window for certain high demand rates, then you do need to buy where you want to stay as tied with my rule of paying cash.
I only used the past as an example of how DVC has been a great buy from 1990-2000 (OKW, BWV, BCV), very good buy from 2000-2010 (SSR, AKV, BLT), and an acceptable buy from 2010 to 2018 (VGF, Poly) or so. I use the concept of how much it cost to join then and what it is worth if you sell today. For anyone that bought over 15 years ago, they are in a great position where their cost pretty much drops to $0 as the resale price is the same or higher than what they paid, so their entire use only cost annual dues (and any finance charges).
To be perfectly honest, the current Riviera prices are shocking and scary to me and I am not certain that this is an affordable option for most people. I have stayed at the resort and it is beautiful, but I greatly prefer VGF or BLT over Riviera. For the points and cost per point, I would also rather take BWV or BCV over RIV as it is so expensive to stay there. Also, the Skyline has been a bust for me as in the morning or park close it is too crowded to be enjoyable, but during the day it is nice.
So, what do I recommend to the original poster - if you can afford spending $36,000 without high interest rates - then BUY it direct from Disney as it gives you exactly what you want. Then spend the next few years enjoying it and if you grow tired of it, sell it for close to breakeven or a slight loss. As I stated before, it generally takes 10 years or so to buy direct from Disney and then sell for a break-even cost (ie. sell for the same price as you bought).
Disney timeshare is not an investment like stocks or bonds or private property, but spending $36,000 requires a full analysis of the pros and cons of what impact to your financial life that will have. If you can't easily afford to miss $36,000 then DO NOT BUY and simply book rooms via
AAA discount or rent points from a member.
Good luck and let us know what you decide.