This May, we will have been members for 7 years: SSR and AKV = 360 points.
Although we have had some great vacations, there are some regrets:
1. SSR - we bought when CDN exchange was still high at 30%. We thought it would go back up to 60%, but instead, it went down. We did not need to buy at all, but we had just returned from baby's first trip -
Disney cruise and 5 days at Disney, so we made an emotional purchase. These points cost us $123.00 per point, so we can never sell them, or we will lose a tremendous amount of money. Although we like SSR, the points are a bit too high, as we love OKW and Boardwalk Standard, and have good luck in getting both of these at 7 months. If this goes away though, we would be perfectly happy at SSR for our approx. 2 week summer stay in a 1 bedroom.
2. AKV - when we bought our contract, the dollar was at 10% so that was pretty good, and resales were pretty much the same price, as we bought when AKV first opened. We bought to secure 1 bedroom values at 11 month, with a split stay with SSR. This brings us to number 3.
3. Split stays - we moved to split stays after our AKV add-on, because we had 175 points and 125 point contracts. Little did we realize that if and when we didn't want to do split stays, this contract at AKV is pretty useless, as you can't get enough nights in a 1 bedroom, so we always would have to do split stays or, borrow from future use year. And we are now here, as we don't want to do anymore split stays, so now we have point issues, and basically our 11 month window is useless for AKV Value room.
4. Point reallocations - they hit us hard, as we go for 2 weeks each summer (occassional March trips thrown in) as I'm a teacher. We then added on 60 more points, as our summer vacation had been messed up. We waited 6 months for a resale to show up, but nothing ever did, so we added on direct. Regret this as we wished we would have known how much we loved OKW, and instead of adding on at AKV 3.5 years ago, we could have saved thousands by adding on at OKW.
6. Dues - because we own 360 points, our dues are high at $1700. If and when our dollar goes down, our dues will be pretty high.
7. Inflated savings - because we got caught up in the long terms savings of owing DVC, and our emotions, we took extra vacations, costing us extra money. We also spent a ton, and I mean a ton on Disney food by eating 2-3 TS meals per day for years. None of this was necessary, and was very different than the way we used to do Disney, before DVC.
Like I said, if we had known then, what we know now, things would be different. We have had amazing memories, but we have shelled out a ton of money over the past few years, and as a young family, this was not wise. We could have had fine vacations with using Disney promos, and saved a ton of money in the process. That being said, for the amount that we pay in dues, having a 1 bedroom villa for approx. 2 weeks is a good value over hotel rooms, as we do prefer to stay on-site. But, as Sammie wonders, should we have put this money into a vacation home instead?
DVC works on your predicting the future, and even me, a person who has had her whole life planned out since she was a toddler, knows that it is impossible to predict the future. Wants, needs, finances, lifestyles, etc. change, and for us, having paid so much for our initial buy-in, we can't sell or risk losing a huge amount of money in the process. And the biggest piece of this puzzle, is that Disney has changed, and will continue to change, and some of those changes, we don't care for. At this point, we are tied to DVC for a lifetime now, and have to make it work the best we can, and what's done is done, but we honestly do have moments where we have regrets...
Tiger
I'm 60 and my DW is a little younger. We are empty nesters and we enjoy going to WDW to be kids again.
and we are thinking about a short trip in May to close out the F&G Festival. We are also hoping to visit Aulani for a week next April.
And over 50,000 in dues to pay.
I wish I had known that many years ago. 
