I think we first started seriously considering it in the mid-00s, around the time we decided we were going to go to Orlando regularly for (my) spring/(the kids) mid-winter break. We considered a 2BR the minimum viable size for the four of us*, and in that season, that meant about 300 points, minimum. Even resale that would have been enough to completely consume our vacation dollars and then some. I took a look via search on the boards, and interestingly enough, the OKW prices in the mid-00s were in the high 70s. I did not feel good about dropping $22K+ in 2006-ish dollars on vacations.
Instead, we bought a Wyndham points deed for about 10% of that, and planned to use it at Bonnet Creek. Along the way I picked up a "stalking horse" trader week for a few hundred bucks to help with using Wyhndham points in RCI. Without planning it, I ended up buying at a resort that was dual-enrolled at both Interval and RCI. At the time DVC was affiliated with Interval, and I was able to grab an exchange into OKW using search-first.
I quickly realized that I needed two traders: One as a stalking horse in RCI, and one for an annual DVC trip in Interval. My wife, quite reasonably, told me to slow my roll on buying a third timeshare in the space of a year, though I kept trying to make my case. That impasse lasted until about day three of that first OKW trip. This was after several offsite stays renting via VRBO. We were walking back from the bus towards the villa. The kids had run up ahead a little ways, and she looked at me and said: "Whatever you have to do to make this happen more often, do it."
That started a 15+ year run exchanging very inexpensvie timeshares for our DVC stays. A lot of those were at OKW/SSR, and there was a period when DVC would only deposit 1BRs. Thankfully, that period coincided with a time when the four of us could not all be in Florida at the same time for spring break, so we didn't need 2BR units. But there were also some gems, including a unit at BCV during late October that I had no business getting. Over the years, I had exchanges at OKW, SSR, VWL/BRV, BLT, BCV, BWV, and AKV-K.
I could have kept that going for a while, but exchnaging takes quite a bit of both patience and flexibility, and I've reached a point in my life where I have more money than patience, so buying seemed to make sense.
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*: We did try a 1BR at OKW for the four of us. Once. Never again.
be going on 2 more WDW trips and 1 DL trip this use year. And if needed we could bank for a year or rent to go somewhere else
