If we only knew then what we know now!
We purchased our Wyndham(Fairfield) timeshare 2 years ago in Pigeon Forge. We purchased from the developer and if I was smarter (I am now) we would have purchased resale. It's much cheaper and we would have gotten the same benefits since we are not VIP anyway. I try not to think about it too much or it will make me sick, but overall we are extremely pleased we did it.
I know many people will say that timeshares don't make financial sense and they probably don't, but we have been on 2 awesome vacations in the last year that we would have never gone on if we hadn't done it.
In October we spent the week at Bonnet Creek in Disney and this was a spectacular resort. We were also able to bring our friends along at no extra cost because we went during "value" time and it cost so few points.
We just got back last week from Ocean Walk in Daytona and it was another great resort. Our kids are getting to see the country (ok, Florida

) and build great memories and we get to cherish those moments too.
My DH did not grow up ever going on vacation and he didn't realize the importance of devoting that time away from life to our family. We both work full time and it does give me peace of mind that at least I know we will be going somewhere as a family every year.
We almost have ours paid off and then I will feel much better, but I don't regret the purchase. The bottom line is if you are going to do it, buy resale.