@WebmasterDoc. Bought in 2004, 2010, and 2013. The 2004 points are gone (SSR), but the other two contracts (both VWL) are still active. Over the years, we've used the points to stay everywhere but Boardwalk, Aulani, and Riviera--though a Riviera stay is coming up in September. Mostly stay at VWL, especially during the holidays. My youngest was four when I bought the SSR contract, and now she doesn't much care to go other than once every few years given she's in college (senior) and about to head off on her own within the next year.
The hardest part over the years was having enough points for the trips we wanted, so borrowing was always a thing. We've taken week-long trips planned several months out and last-minute ones for just a couple of days. By the time I bought in, I had retired (military), though I've never actually stopped "working." At first, it was all about the parks, and gosh, it was nice to have marvelous accommodations with some nice perks. Over the years, the perks have largely gone away; the discounts have lessened; and the parks have become too crowded. So, now we largely go to enjoy the Disney moments that still exist, especially at places like WL: marvelous theming, gorgeous architecture, and little Disney touches. Do we hit the parks? Sure, but if we do five rides over three days, that's considered "a lot."
With that in mind, we no longer plan long trips--four days max. Disney Springs is almost as big of a draw as the parks, certainly better eats overall. One reason for that attitude is that we, too, moved to HHI. We can slip down to WDW in just over five hours, but we already live in a lovely vacation place where we enjoy the Disney dust. We didn't do the rent, condo, buy pattern; instead, after visiting here five times over six years during the summer, it became the spot we focused on to settle down. I was still involved in other activities where we moved from, including teaching high school, but when Covid shut us down, the timing just seemed right. We began looking in earnest at houses here well over a year ago, and once committed, realized how hot the market was. We visited a couple of times in the spring of '20, finally found a place that didn't disappear from the MLS listing overnight, made an offer, and put our own house on the market. Three weeks later, we had an offer on our house.
Fast forward six weeks or so, and we rented a truck, packed up, and took off the following day around 6 a.m. The drive was a touch over five hours. After a quick lunch, we closed on our old house, then two hours later, closed on the house we were moving into. What a day! Been here nine months and love it. The points we own are great to use for a quick trip down to WDW, and while we own APs, they don't drive our trips. We both work part-time, and when we feel like it, we head down, enjoy a few days, and come back. Long gone are the days we're going to spend hours upon hours in the park and spend money in shops or stores. In fact, the inventory offered by Disney any more is boring, generic, and overpriced.
In essence, we help Disney's bottom line by owning DVC, having APs, and the occasional tchotchkes. But, they'll never get us back to the parks the way we used to visit--again, too crowded, too little actual value for things like paid events, and too generic. We've not abandoned Disney, but we've decided they are now a distant relative. Great thread, by the way!