Wow!!! We were rival High Schools! Not really.... I went to CD East Jr High and all of my best buddies went to CD. I was just on the other side of the line and therefore went to East. It was a bummer for me, but I managed. I graduated in 88, just 6 yrs behind you.
I LOVE the VWL theming and wanted to buy there, but the timing wasn't good and my husband decided to invest that money in the mkt instead (it's all gone by the way). Then I fell in love w/ the BCV and their clean and bright theming and their closeness to EPCOT, but the maintenance fees scared my husband off and we figured we would just pay as we go. Then we had kids. And we found out just how important it was to have the appliances w/ little ones. We read the financial reports posted and decided it WAS the right time for us.
We decided on SSR because of several reasons: the decor and coloring (green walls, granite looking countertops, and dark woods) is just like my home in PA, and the extension in the deed to 50 yrs helped (even though we'll be very old by then), and the rebate of $10 a point if bought by the 31st clinched the deal. We don't mind liveliness so Downtown Disney is fine w/ us. And the pool theming sounds awesome. And I figured we can always stay at the appropriate
DVC resort as our kids grow. Maybe while they are young we'll stay at VWL and vist the MK or at the BCV so we can walk to MGM to see Buzzy and Woody. Then when they are in their teens stay at Saratoga and do Disney Quest as you will be doing w/ your son. I think Saratoga looks incredible and I am sure I won't regret buying there, but I was so happy to just become a member, I don't think I would've cared where we bought. Didn't matter to me and according the DIS, they are all wonderful. Thanks for contacting me. I hope I answered your questions.