Possible Solution for Captain Kidd
We struggled with the DVC question for years. In fact, we got started on our due diligence in 2007, and I have the "Dreams" hard cover book that shows AKL as being under construction with concept art, etc.
It was not until this time last year that we finally decided to buy in. It was a difficult decision, in no small part because we very much prefer to stay on property but had never stayed in a deluxe resort. We had no problem staying at Pop Century, figuring we would be in the parks most of the time anyway. However, we absolutely loved the Epcot Resorts area and daydreamed about the added space of a villa and the ability to walk or ride a boat to two of the parks.
Ultimately, we bought resale at Boardwalk Villas. We bought 240 points (with 240 points banked from 2010), at $67 per point. The cost was just north of $17,500.00, after factoring in the closing costs and up front annual dues. My math was not terribly complex. I divided that $17,500 by 31 years to get a "purchase price" of about $575 per year. Adding in the annual dues of approximately $1,350.00 per year (without taking into account inflationary pressures), we are looking at around $1,925 per year. For that price, we can stay at the Boardwalk in a 2BR Villa for 5-6 nights per year.
Our first trip as members was in November, and it is difficult to articulate the feeling we had pulling in and knowing we could come back again for years to come. It also is difficult to place a value on how a villa can reduce the stress in the family by giving everyone some extra elbow room.
On top of that, we have been able to bank points, such that we plan to spend 4 nights in a 2BR at the Grand Californian Villas next spring break, while still being able to take our November trip to the Boardwalk. We will continue to go to WDW in November and bank points, and then we plan to hit Aulani for a week in a garden view room in about 3 years (by borrowing points). In the 4 years after the Aulani trip, we will have to do some borrowing to take our November trips, but we will be back to banking after that. The CA and HI trips are things we likely would not have even considered without having found a good resale contract with a full year of banked points.
Believe it or not, for us one of the appealing aspects of the Boardwalk was the fact that the contract expires in 2042. In other words, our commitment to the annual dues is for only 30 years. Captainkidd, you would be in the same situation buying resale at Wilderness Lodge. Would that help with the anxiety over locking in to DVC for an extended period of time?
Trust me, I was with you on the cost-benefit analysis for a very long time. However, my sense is that if you feel you can find a good deal on points, you will be happy with the purchase.