This may be a long post. We started with 200 OKW points. Bought cheapest WDW resale at the time...May 2006. We wanted the most points our money could get. We initially planned to go 1-2 times a year and get a 1BR and picking different resorts at the 7 month window to try everything out. Kids were in year round school so we planned to go during off season intersessions like in September. We have stayed at OKW twice and like it just fine but it's at the bottom of our preference list. We have been able to use our OKW at every east coast
DVC except VGF and Poly but we haven't tried to stay at those and might not due to high point cost.
Our three kiddos became teens and we needed to upgrade to 2BR villas. So we added more points and went with HHI because they too were cheaper contracts via resale. Plus we figured we could save money every other year by doing beach trips...no park tickets needed or airfare as HHI was easier drive for us. We had one HHI trip under our belts and loved it there and it was one of the tougher to get resies at 7 months out (using our OKW points). Nice to own HHI for summer trips there. Added 50 and 25 HHI points for cheap...$50pp.
Then we went to add some more HHI points and were in ROFR when the sellers cancelled on us. We were also planning a big family Xmas trip to WDW and SIL, owner of AKV points, wanted to book AKV. It was always my dream resort since our very first Disney trip in 2003. So on impulse buy we jumped on a loaded 100 AKV contract for pretty cheap...$66pp. We booked rooms for 3 families at Xmas with that loaded contract. But within two years we realized that we could use our OKW to book at AKV, no problem. And when resale prices skyrocketed we listed it and sold that very day, for $80pp. We did end up adding 50 more HHI points too.
Between buying and then reselling the AKV contract we also added on at BWV. We had started going to F&W every year and wanted an Epcot resort for those trips. You really have to own at one of those if you want to book for F&W time. We calculated what we'd need to book a few weeknights in a standard view studio and figured 55 would be enough. We went on WL for both our UY...we have two UY. We could have got BWV or BCV at the same price and they offered a $7pp off deal for any add ons over 50 points. We chose BWV to be able to save points with the standard view category. Our June UY came through and then two months later we got a call that they forgot to take us off Aug UY WL and those were available if we wanted. We took 25 of those, couldn't resist. As it turns out, that was a good decision because it is hard to get standard view studios for F&W even as an owner who books exactly on the 11 month window. So we end up with P/G view or 1BR villas, which we prefer 1BRs anyway. Also glad we went with BWV over BCV now that BCV has removed the jetted tubs and ceiling fans from the 1/2BR villas.
So, now we have 3 resorts, 2 UY, 405 points in 6 contracts. We use HHI and BWV almost exclusively at those resorts. We use OKW all over. We like AKV, VWL, BWV and BCV as well as HHI. We have enough points total, but wish we had more at BWV...like 30-45 more. And wish we had VWL. If only we could trade our OKW for more BWV and some VWL....