I took 3 years from deciding that I was probably going to buy and buying. Part of that was waiting for prices to fall until that math worked as well as I wanted it to, which thankfully they did, part of that was making sure I had confidence in the UY I wanted to buy, and part of that was making absolutely sure I was not going need the cash I was going to spend on it for something else.
We did 3 Disney trips in the interim, staying at AoA, WL, and Hyatt House Anaheim (on points). AoA reinforced for me that that wasn’t going to work well enough for us, and WL reinforced that I NEEDED the 1BR space because Disney rooms are too damn small. Which in turn reinforced how much I needed prices to fall to make the math work, because 1BR math was upside down last year.
On that trip we also saw Saratoga Springs in person, taking a tour and generally getting a feel for the place. That gave me the confidence to be happy to stay there if I needed to.
We ended up buying a loaded SSR contract at $83/point, probably a little less than I would have gotten it for in spring 2020 when I first seriously considered buying, and far less than I would have paid the year prior. We more than paid for the AoA and WL stays with the savings vs 2022 prices.
In the mean time I fully educated myself and got myself into a way better position to buy. Happy as hell that I waited 3 years.