I don't necessarily regret buying in, but I wish I'd done more legwork before we did. We took a trip with the kids, stayed at Boardwalk, learned about
DVC from a guy at the pool, came home, and bought a large contract at SSR. I didn't know about the DIS or the resale market and admittedly didn't do much research.
If I had it to do all over again, knowing what I know now, I would have shopped around and bought a few smaller contracts via the resale market for the 11 month booking advantage. I don't necessarily have a problem with SSR, but there are other places we would like to stay, and we have encountered some difficulty getting in.
I also have a distinct longing to stay at the Monorail resorts, but feel like that avenue is closed to us because we've chosen to spend our Disney money in another way. I know that whatever is going on at the Contemporary may help, but who knows what sort of availability issues they'll have there.
And my last issue is this...no flames please...after our last trip, I am worried that going to Disney every year, sometimes twice a year, is taking the magic out of it. My kids were so blase' about it all, and I found myself feeling sort of "been there, done that" as well. It sounds blasphemous coming out of my mouth, because I LOVE Disney. Now I'm worried that too much of it is making it less special.
So...regret is a strong word. No, I don't regret having done it. But I have my worries.