We started with 200 OKW in 2006. Our kids were 7, 7 and 9. We got 1BR villas for a while. We lived in NC and my kids were in year round school so we planned to go every Sept. We first used our points in Sept of 2006 and had a great time...then in 2007 we moved to MD and our kids were in traditional school so no more Sept trips. And likely no more annual trips since the drive would be so LONG and flying would be so EXPENSIVE for 5. MIL and FIL were going to WDW every Jan. So they asked to buy half our points. They basically own the OKW contract with us.
Then, 2011 came and my kids were now big 12, 12 and 14 year olds who liked their own space and would fight a lot. Also needed another bathroom. So we began getting a 2BR. We needed more points and we thought HH would be nice since we could drive there more easily plus we could save money on trips there since we'd not have to get park tickets. In 2012 we added on 75 HH points. The plan was an every three years plan with HHI one year (using banked and borrowed for 3 years of HH points) and WDW one year (also banking and borrowing for 3 years of points) and cruising one year. That WAS the plan.
BUT then we started to buy an AP or PAP (once with regular
DVC pricing and then twice with DVC special offers) and started getting TIW card. We felt the need to get in a few trips on each AP and TIW. The more days we used them the better so we started to take a few trips each year. In 2013, we discovered F&W. So we needed MORE points. In 2013 we added 100 AKV points and 50 more HH points. But we also knew we wanted to make F&W a regular trip so, in 2014, we added 80 BWV points. That brought us to 505 points. I was looking for a 5th resort, a MK area resort when DH said enough is enough

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Meantime, FP+ rolled out and we are beginning to detest all the planning. And we are finding the parks getting more and more crowded. Plus our DS is now off to college and griping 'no more Disney' and DDs are busy with finishing HS and playing travel softball. We decided to stop getting an AP or PAP and to cut back the trips. We also realized we didn't need to own at AKV to book there (we could use our OKW points). Resale prices being high, we decided to sell the 100 AKV to make a profit (got those college bills coming in now). The contract closed and the points were removed from our account about a week or 2 ago

(bittersweet). I think our 405 points (less the 100 points MIL and FIL use) is good and will get us the trips we want. We're thinking January trips (in 1BR BLT or AKV) with whichever kids want to come and F&W trips (in 1BR BWV) for just DH and I.