The OP really made me stop and think back to the 90s and even early 2000s. Back in the day, it was a lot easier to get ready for vacation. It's interesting that back then room reservations were made by calling the 800 number, tickets were purchased the same way, and ditto for the dining reservations. Often you didn't have to wait on hold for someone to pick up and rarely was it more than 15 minutes. The person who took the call could complete everything reliably in maybe 10 minutes. They didn't hang, or crash

. It's pretty bad that technology, coupled with policy changes, has made it way harder, more involved, and takes much more time than the human-intensive way of the past.
Back then, we also had free choice the morning of as to which resort to visit. Weather is cold, let's do MK today and we'll go to Typhoon Lagoon on Thursday when it warms back up, for example. We were still planners, carefully reading both the Unofficial Guide and Burnbaum, and developing each park's plan, but that anticipation of the vacation during planning was itself fun. And, we had the plan for which rides to do first and the order we would get fast passes on whatever day we ended up in that park.
Now, I swear it takes me way longer and it's way harder to successfully get the vacation set up using the technology given us, and forget about trying to get a human to help these days. In making operations cheaper (for Disney), they have made it way harder and frustrating for the guest. Fold in all the long-lived (unaddressed) bugs and the technology actually interferes with the "story". It took Disney literally years from the time it was first rolled out to get something as simple as online check in to be reliable. Forget about the fiasco rolling out magic bands and
MDE.
The required park reservations still make it impossible (or at least risky depending on the week) to swap days around last minute during the trip. But, I'm really hoping
Genie+ (despite the fee and current technology issues) gets us closer to the days of paper fast passes, when we tended to get on a lot more of the rides we wanted and weren't distracted from enjoying the story.