I think I am going to look into resale AKV!Somewhat duplicate but I'll add my take. As noted, do not buy VB unless you want to stay there routinely. It's cheaper per point but more on dues and in the long haul, that will cost more than the lower cost would save. Plus if WDW is the goal you'd always have to wait until the 7 month window. SSR is the best value and it's only 3 years less than AKV. It also has lower dues than AKV and along with BLT, the lowest of the system with both likely staying lower and I suspect, advancing at a slightly lower pace. For WDW SSR will be the best value just to get into the system, BLT will be second with AKV likely third. The off property options can be useful but again, only if on intends to use them a fair portion of the time. The best off property values $$$ wise will be Aulani or VB with a subsidized contract or HHI. I would not buy OKW unless one wants a 3 BR there most of the time because of the higher dues, shorter expiration and the risk of the transition from the 2042 expiration to the 2057 group.
There can be a point depending on how you'd use it. I would not buy without a fair amount of experience in at least 2 of 3 areas (DVC, Disney deluxe, timeshares in general). The more knowledge and experience the better but obviously one has given up savings by delaying too far into the game. I would not buy planning to go every few years. I think EOY is workable but every third year questionable at best. Plus the savings of buying for less trips is less as well. Things are at a high right now and there will be a pullback in price at some point though when and whether it's worth waiting is unknown. IMO the biggest issue is whether to buy DVC at all but after that the choice of home resort, UY & # of points is still VERY important. MOST people buying in initially make significant mistakes. They buy too few or too many points, they overpay by getting the newer most expensive resorts, they buy retail when they shouldn't and they rarely know enough to make good decisions. The exceptions are few but include people that have a ton of experience in the areas I mentioned, former DVC members, and those with a significant exposure to the system from family/friends. While some uncertainty will always be present, once one is sufficiently educated AND has the appropriate level of experience, they should KNOW what's best for them not just think they know. Statements like, this was our first trip or I've always wanted to stay at X resort so that's where I bought instantly tell you they did not make an informed decision and they're chance of it being a good one in their situation is low but they might luck out.
But there still a real cost to do so in the range of10 to 15% of the previous cost
IMO that it's discretionary spending/vacation doesn't give one a pass on the goal to make good decisions with finances. And depending on the choices made it may not be $2000 but $10K for a retail purchase. IMO the car example is a good one but likely not how you're thinking, buying a new car and deciding in a year you don't like it and then sell it to buy something else is possible but just as poor a choice financially. While one can't truly predict what the future will hold, many of the issues can be anticipated if one just puts in the long term thinking. Retirement, possible job changes, kids in activities and can't travel, I won't go as much as I think I will, and I won't like the resort I thought I would are all things that can and should be considered.
Looking at dues alone there is a significant long term cost for AKV over SSR. The last time I compared all the numbers it was 20% more over like 30 assuming equal inflation. If one uses value at AKV that changes the numbers but the last time I did it was before the change in booking categories which also changes the numbers. While you might personally be talking about variations at entry level, many looking at buying in talk themselves into poor choices. The way I answer such questions is to the masses as well.
I'm Chairman's (top VIP) with Marriott with 16 weeks total, Platinum with Bluegreen (their highest VIP) with over 100,000 points and own a small amount each of an RCI points resort, Mx week (points individual resort) & Wyndham Points plus 433 points with DVC down from 885 years ago. Bought DVC likely as the first non family resale buyer if not the first true resale buyer period back in 1994 and Marriott fairly shortly thereafter. I've seen a lot come through, especially with DVC, and seen a lot of people waste lots of money, often 5 figures worth buying things that won't work how they envision. There are few things better than Disney at separating people from their money making poor decisions they feel great about. I've also sold some timeshares over the years, including a couple of Marriott, chunk of DVC points all at OKW, a second contract at the MX resort and several fixed week/fixed units at an Aruba resort. Thus I consider myself more educated than most for Bluegreen, Marriott, DVC and Interval/RCI esp. And my greatest area of knowledge and experience is with DVC. I've made a lot of good choices, sometimes by chance and avoided a lot of potential mistakes, also sometimes by chance. For example, the Aruba resort I mentioned was the one I both bought and sold weeks then later bought weeks which I ended up converting to Bluegreen. They had 3 special assessments while I was involved but by chance I missed the first 2 because I didn't own at weeks at the time of the SA and the last I missed most of it because I'd converted to BG points and the SA was spread over a very large group of people. That one would have been $10K had I not lucked out.
Obviously there are variables, SSR is not the same as VGF for example. So one who has a number of trips under their belt ON PROPERTY and is well aware of the actual DVC resorts and who has a clear understanding of their goals over say the next 7-10 years should be able to make good decisions. Whether they will or not would remain to be seen. I referenced some of the common mistakes I've seen above. But there does come a time when one has to fish or cut bait. I've also seen posts from people who have looked at DVC for a decade or more who clearly are (and were) good candidates for DVC membership and haven't bought. But the issue is that the savings they've given up is minor compared to the impact for some of mistakes. Things like not only financing a timeshare but putting one's home at risk to do so. As I said, I often post to those reading now or in the future as much or more than to the specific post or person I'm replying to. So while you and I might quibble about whether we should buy SSR, AKV, BWV or BLT all resale for example; the ultimate decision for an individual may impact both their financial well-being and their usage/enjoyment of what they own. There are clearly situations where buying top or bottom or in between is best and where buying retail is best. But one who buys say VGF retail and uses at other locations most of the time literally spent an extra $10-15K they didn't need to AND they may not be able to use it how they want/envision. And that $10K will be $50K when one looks at what they could have done with the extra funds that were wasted. We don't want make perfect the enemy of good but we want to avoid as many mistakes and make as good choices as possible.
Dean's advice years ago on the Dis boards gave me the courage and information to buy our first Marriott.
That's the beauty of places like TUG, the group mentality to help each other. We each bring something to the table.
So you obviously are a fan of TS! 
Do you mostly rent, or are you semi-retired making the rounds of all those fabulous TS you have? 
