Bought our first contract via resale in 2006. Our kids were young and money was tight so we went with which WDW resort where we could get the most points for our money at that time and that was OKW. We have found OKW to be our least favorite.
Then we needed to add more points, once our three kids were hitting teen years, so we could move up from 1BR to 2BR stays. We stayed, with our OKW points, at HHI and really enjoyed it and liked that we could use
DVC without buying park tickets or dining plan or airfare (was living in MD where we would fly to WDW but could manage drive to HHI). Plus the added bonus was that HHI points were some of the cheapest....so in 2012 we bought 25 and 50 pointers from the same seller. We figured we could use them at WDW at 7 months out or when we wanted to skip buying park tickets, and all that, we could book HHI. The one time we used OKW points there, July 2009, it was hard to get at 7 months out. We had to shift our dates and then could only get 4 nights. So, you need to own HHI if you want to stay in summer months and some holiday times or if you want a 3BR GV.
Then, in Jan 2013, we wanted to add more HHI points as the 75 wouldn't get us far (maybe a short stay every three years). We found and went to ROFR on an 88 point resale. The sellers backed out after 9 days in ROFR. At that same time my in-laws were all discussing a big family Xmas trip that year. SIL owns AKV and wanted us to stay there. A loaded 100 point AKV for a great price popped up and we did an impulse buy in our frenzy after the HHI contract fell through. We closed on the AKV two months later and immediately booked rooms for us, MIL and other SIL for Xmas before the 7 month window opened.
Then, later in 2013, we saw a great 50 point HHI resale and grabbed that up too.
Also in 2013, DH and I went to our first F&W sans kids. We managed to get three nights at BLT. We fell in love with F&W and started an annual trip. But we saw folks walking in and out of the IG to get to F&W and we really really wanted to do that. A little research and trying to book for 2014 told us that it would be best to own at BCV or BWV. So in 2014 we called guide and went on WL for 55 points at BWV. We decided there over BCV because we could save points by booking standard view so those 55 points could go farther. We went on WL for both our UY, June and August and got June in 2 weeks. Then two months later, our guide called and said they also had the Aug points if we wanted them. We could not resist 25 points more. That was 2014.
In 2015 resale prices were skyrocketing. And we noticed we could book AKV with our OKW points at 7 month window. So we resold our AKV and got $15pp more than we paid. And we had stripped it, using through 2016. So we used five years of points and made money on sale but paid commissions and 3 or 4 years of annual dues... So maybe a wash.
In 2016 we called guide a few days before DH's birthday and our 20th Anniversary (same day) and was surprised to find they had 25 Aug UY BWV. So we got those as a gift for DH. We had found having our BWV points in two UY a bit of a pain so adding these 25 more to Aug helped. We can just book from one UY instead of trying to transfer or book separate and link.
At 200 OKW, 125 HHI and 105 BWV. We use HHI mostly at HHI and BWV mostly at BWV. OKW we use wherever we can at the 7 month mark. We have preferences and we go down the list and then stalk the RAT and make waitlists. But we are happy to stay at any. We like things about all of them. And kinda like changing things up (instead of always staying at same place). But, in the spring, we were back on the hunt for more points. When CCV went for sale, I wanted to buy 70 points there so badly....for Xmas stays. But the hubby just could not swallow the price pp and annual dues cost. He pointed out that we could get double points via resale. So we offered and went to ROFR on 150 HHI. But it got taken by the mouse. We made another offer on a HHI and the sellers refused to budge on price. So we switched over to 150 BWV contract and got it. Now we have a total of 255 there. We are good.
I wouldn't mind a MK resort but not thinking that will happen. I would even sell the OKW to buy a MK resort but DH would never agree. He says 'why pay money to sell and then buy less points at another resort?'.