So you've gotten a ton of answers - and I haven't read the whole thread. The truth is that
DVC isn't for everyone. We were a moderate family (with occasional value stay) that could never justify a direct DVC purchase even though we went once a year. We would normally travel with free dining as well.
At the time we bought (2014) we saw an opportunity to "value proof" our trips a bit with a DVC contract. We bought at AKV - and we can typically get a standard view studio room at our home resort which run us typically $120-150 per night, which is averaging the buy-in across the life of the contract, plus maintenance fees. Buying Riviera Direct hits a MUCH higher price point with the
point charts - more like $250-300 / night for a studio - but there are still bargains on the resale market.
The difference is it has made our vacations MUCH more relaxed and now having stayed at Deluxe resorts for the last 5 years at what I would call moderate prices we feel the investment was well worth it. Not everyone would consider it. It IS a luxury decision. But for a $15,000 buy-in at Saratoga resale you can get 150 points for the next 35 years which would typically give you a week each year with a MF around $900. The opportunity there is to not just stay at SSR but other deluxes. If in 10 years you don't want to do it anymore - you can likely sell your contract for around the price you paid.
Suggest watching some episodes of the DVC show on the DISunplugged, which talks about the pros and cons of DVC resale and direct. I'm not going to tell you DVC is right for you, only you can decide that. If you are looking for cheap Disney stays you are better off staying value or if you want a bigger room you can stay off-site and save a LOT of money. DVC isn't really a money saver unless you look at versus Moderate and Deluxe stays and even then it is a long-term savings, not a short term savings.
In my view it's similar to saying: "I can live in an apartment for $1600 a month, why would I buy a house where I have to put $20,000 down and then pay $1200 a month for a mortgage." Not an exact analogy as there's a lot of other arguments for a home, and we are talking about a vacation versus a necessity - but still that's a way to think.