We first took our kids to WDW in 2003 when they were 4, 4 and 6 (DH and I were 30). We lived in NC and the 9 hour drive wasn't bad. We stayed off site. I didn't want to go and DH planned the trip...we had a great time and I fell in love. We went again in 2005 and stayed on site at POR and got the DP. Wow, that trip was even more magical. We went home and looked into DVC and bought 200 OKW points via resale in 2006 to go for a week every year. We bought the cheapest WDW resort buy in at the time so that we could get the most points for our money (SSR was selling new at @ $98/point...we bought OKW for $76/point). Our 1st trip as DVC members was at BWV in Sept 2006...we took my mom and our 3 kids (7, 7 and 9 by then). Boy did we LOVE BWV...it's still up there on our list.
We moved to MD in 2007 and didn't think we'd continue to go to WDW every year since the drive was so far and flying for 5 was (and is) so expensive. We debated selling but MIL/FIL came up with the idea to pay us for 1/2 our points (so they could use 100 every year...they had started going every January). We took them up on that but soon would discover that we would still use a lot of points each year. So we added 75 HHI points in 2012. The plan was to alternate years with WDW and HHI. We found that we still needed more points (I think because we went from doing 1BRs to 2BRs once our 3 kids became teens). So, around Dec 2012 we looked at adding on a few more HHI points. We ended up adding on 100 AKV and then 50 HHI points...long story. And I was still looking for about 30-50 BCV or BWV points for F&W trips.
So, now at 40, we have a ton of points and can get APs every other year to do 2-3 WDW trips...and then do DVC beach trips the other years (non-WDW years)...we started this plan, by accident in 2009, and were thinking we'd continue. MIL and FIL were still going...we did a couple Xmas trips with them and SIL1 who is also DVC member and used our points for SIL2 to come as well. We figured that (big family Xmas trips) would fall into our every other year plan. NOT!!! This last Xmas trip went so poorly (family issues not Disney issues...another long story) that it was the LAST big family trip to WDW. And we also found that our teens have become so miserable on these trips (don't want to go...are "bored" and complain a lot). Now we are rethinking how we use our DVC and we were thinking we'd sell some points. But I think we'll hang onto them...we'll find ways to use them for the next couple years (sans teens...at least sans DS-17) and then I figure the children will come back to the mouse (once they are with significant others of their own and are a bit grown and interested in nice family vacations again...then, down the line, we'll have grandkids to take).
Edit to add: The draw to buy DVC was that 5 of us in a regular WDW room was tight and expensive, so we likely wouldn't go so often. We love the villas having a master bedroom for mom and dad to be separated from kiddos. The washer/dryer and jetted tub is a big draw too. The kitchen, not really needed for us. We started with 1BRs and would drive so we could take an airbed for DS (the girls would have the pull-out). Around the time we started flying (Dec 2011), we also started getting 2BRs so DS would have the pull-out and DDs would have the 2nd bedroom. Now, I think we'll go back to 1BRs since I doubt DS will come with us anymore. And DH wants to go back to driving as well, so we could always throw an airbed into the car if DS decides to join us. DH and I did our 1st F&W and our 1st studio in Oct...it was also our 1st stay at BLT and we loved the studio there. So, if the girls don't go with us either, we'll be fine with a studio. MIL and FIL get a 1BR...MIL likes to sleep in and FIL is up at 5:30, so he can go out in the living room and let her sleep in.