We bought directly from Disney (150 points at SSR) this past June. We (19-year-old son and I) went to the presentation on the last day of our vacation; we were given 3 days from the day we returned home to take advantage of one of two incentives: $93/point ($8/point credit) and we got all 150 points for 2006, or $87/point ($13/point credit) and we wouldn't get any points til 2007 (w/a Feb use year). We chose to get current points.
I took all 3 days to decide. Read Disboards (thanks to my son who found it for me); asked a zillion questions of my guide (Tim Grabman--he's WONDERFUL!) at Disney...
For me, the complete convenience/ease of going through Disney--and the sense of trust I felt in dealing with Tim--was one of the two major reasons I chose to buy through Disney (we paid about $7/point more than the "going rate" for SSR at resale). The other major reason was that we plan to go to Disney every Thanksgiving, and I wanted to make 2006 Thanksgiving reservations right away.
I can't say that I was "emotionally" aware of availability issues. To be fair, Tim told me about them...he told me that T-giving (and other holidays) are popular
DVC times and that we might need the 11-month window to get to stay where we want to stay at T-giving (he also made it clear we could buy our 150 points (more more) at any other resort; he did not "insist" on SSR)...and he also noted we might have trouble getting T-giving reservations (we were five months out at the time). I didn't quite believe him...like many others, I was used to going thru CRO and I knew there was plenty of availability for T-giving in June...it took some "experience" to fully understand the truth of what Tim told me--that DVC reservations and "regular Disney" reservations are entirely separate!
In any case, he advised me to use the wait list; I did and we got our T-giving reservations with no problem--took about 5 weeks to get the 2 days that were not available on the day I called first...
On the third day after we got home, I gave Tim my credit card number to pay for our purchase (we didn't finance)...an hour later I made our first reservations. Two days before the paperwork arrived.
Reading through all the paperwork (something I felt compelled to do) was a pain--and the ONLY "pain" in the process. Everything else was incredibly smooth and easy ... Tim, MS, and the people who handle the paperwork were wonderful about answering my "mountains" of questions...and MS has been wonderful about walking me through my early efforts at making reservations (we've planned three trips so far...I've used up all our 2006 points, and 2/3 of our 2007 points...but I refuse to even consider succumbing to "add-on-itis" until we've actually taken our first DVC vacation! And that's T-giving, 2006...)
From reading Disboards, it sounds like buying resale thru the Timeshare Store is just as easy, altho it takes longer. And now as I understand it new buyers have to pay closing costs, whether thru Disney or thru TTS...Disney paid our closing costs.
For us, the convenience and ease and sense of "being taken care of"--at a time when I was still learning the system, made it totally worth buying thru Disney. Whether I'll feel that way if and when I want to add on remains to be seen. It's hard to overrate "trust" and in the 18 years we've been regular WDW visitors, I've grown to "trust" Disney (yes, I know it's a big corporation whose purpose is to make money...but I've been treated extraordinarily well by Disney, under lots of different circumstances--when there were problems that had to be solved as well as when all things went exactly as planned). Whether TTS (which is where I'll go if I decide to try resale) will inspire my trust at a level where the savings in acquisition cost outweights my peace of mind with respect to a big chunk of money is something I just don't know yet.
Good luck in making your decision! Hope this story of our experience is helpful to you...