Okay--here are my questions:
1. Is it really as easy to get the dates you want as people say it is?
Typical MBA answer...it depends. There are some periods at some resorts where booking at 11 months is necessary. There are some accommodations or views where booking at 11 months is necessary. In particular, ANY WDW resort from Thanksgiving through New Years is going to be very difficult to get unless you call right at 11 months. Also, the two Epcot resorts are difficult to get during Food & Wine Festival.
On the other hand, our extended family has made 30 trips in the last 5 years (3 families sharing a DVC account in a family trust) and only one of those was booked during the 11 month window. That one was an early December trip, and you definitely have to call right at 11 months for those.
Most of my daughters' trips were booked 3-5 months out, some absolutely last minute -- but for last minute you have to be willing to be disappointed, and you have to be flexible about accommodations, resorts, dates, etc. We all live in Miami, so that's no problem for us. If you're flying your family in, that's a different situation.
2. Is it hard to get dates at other locations that aren't at the Disney resorts?
Depends on what you mean. If you are talking about RCI exchanges, yes, that's difficult and uncertain, but doable. Keep in mind that using DVC points outside of DVC is a) not usually a very cost/value-effective use and b) the ability to use points outside of DVC is not guaranteed and could go away with a stroke of the Mouse's pen.
For timeshare exchanges outside DVC, there are several other timeshare programs that offer the full spectrum of options, cost far less than DVC, and trade better than DVC. Some can literally be purchased on eBay for $1, sometimes with free closing.
3. Does anyone know if there is a plan for what happens when the timeshares expire?
There is no current plan that anyone knows about.
4. Are you happy with the DVC? Why or why not?
Like any timeshare system owned over time, there are going to be things you like and things you wish were different. We are very happy with our DVC ownership, despite occasional frustrations with DVC management on individual issues.
5. Is there any reason not to get resale properties?
Only three legitimate reasons that I can think of:
- You absolutely NEED to finance your purchase and have no more attractive alternative than paying 10.75% or 14.25% interest to Disney.
- You would feel deprived by missing the prestige of having paid 25-40% too much for your DVC.
- You just absolutely, positively HAVE TO HAVE ownership at a DVC resort where there are currently no resales -- Aulani, for example. Personally, if I were in that boat, I'd use some other method of going to Hawaii and wait a year or so for a resale...but that's just me.
ETA: We've bought both ways. We bought our first contract resale and saved $4,000+. We bought our second contract direct on a great promotion for what was actually a little better price than we could get resale. (Those days are GONE.)