The reason for all this change and the need for planning is 20million visitors to the Magic Kingdom alone. That is significantly more people than 16years ago.
And those lower numbers of people who loved winging it came home and told their friends about their awesome trip, and they told two friends, and they told two friends, and now EVERYONE is going to WDW and now one *has to* plan (even if you're planning to not plan).
To answer your question, a normal person would plan to book a dinner the day of the dinner, or maybe the day before. A normal person would never assume they need to book any dinner six months in advance unless they were going to one of maybe 25 or 30 restaurants in the country. The ADR situation at WDW is what it is, but it is not normal.
It is also not normal to compare having a meal at a theme park with getting tickets for the most in-demand Broadway show in recent history. Most people do not think of concert or show tickets as the same as a theme park meal. That is the weird thinking that comes with being "into" Disney World, it isn't normal thinking.
I don't think I think abnormally about travel. But when I see that a place opens reservations 180 days out I think "there's a reason for that; I should probably do that". Now, it's easy for us because we are vegetarian and therefore our choices are limited and it's pretty easy.
There are more people wanting to visit BOG on a given day than might see a show for Hamilton (unless I'm overcounting how many people can be seated in a whole day of BOG and undercounting how many people fit in the theater where it's showing), so the competition is more fierce. To me, it's going to be HARDER to get in for the meal. I mean, if I'm traveling for Hamilton, I won't make my plane reservations until I have that ticket.
It's counterintuitive actually, as a trip to an amusement park really shouldn't be hard to plan.
I disagree. I really don't like waiting in line for a 30 second roller coaster, and so I plan. I plan when going to our local park (Wild Waves) so that I don't have to wait for ages. I look at their website, I see if there are any venues where we might find something palatable. I see if they allow water or snacks. etc etc etc.
We didn't plan back in the early 80s for the then-Marriott's Great America, but that's because we went often and knew where everything was. And when you're going with fellow middle school buddies, waiting in lines isn't as awful as it feels when dealing with your own family.
If I left the planning to my husband, we would eat all counter meals and go on whatever rides we could manage to wait for. He just wouldn't plan. It isn't in his DNA. My son asked to see my plan and then said "I like this. All planned out. I hate standing around wondering what next. " almost cried!

We've gone through a process with that! First trip (day trip) to
Disneyland I made a plan! I was teased mercilessly by my brother for it. I finally put it away and magically came up with the answer to "what do you want to do next?" We kept following my plan, but no one saw me reading my list. Second day trip was the same, though I never took the list out. I just was always the "hey we should do this next" person whenever someone tried to take out a map or stop in the middle of the "road". The next trips were mainly just with hubby and son, and they'd better not tease me even if they are thinking it in their heads. And finally they saw the difference between what happens when we wing it vs when we follow a basic plan. And they like the plan better. They don't like the process, but they like the result.
But OUR personalities don't mesh well with winging it. One or more of us generally has something in mind, and if that isn't discussed and somewhat planned for, if we happen to miss it, it's not good. We get too sad. So it's best that WE *do* plan to at least some extent.
Awwwww... I miss Mr. Toad's!!!!!!

It was actually one of my favorites. I know that I'm probably in the minority there.
I don't think you're in the minority at all. Remember, they kept it at Disneyland. It's a "must do" for us every time.
Haha, we're "unplanners". We decide to go somewhere, book a place, do some minor searching on local attractions, but mostly just go. We wake up and see what we feel like doing. Drive and see what we find

Needless to say, once I joined this forum, I had my eyes opened to the other side of vacation planning, wow. In all honesty, I'm not a fan. I prefer more relaxed, spur of the moment vacations, we both do. But, I'm willing to sacrifice that for Disney
As long as there are no complaints if something is missed, that works well! It's good to know your family's personality. For us, it's the opposite. It takes an amendment to the Constitution to get us to agree to wing it and to truly take what comes for that day. It's serious work to get our minds there. Or rather, it takes work to get our minds to be OK with what happens during that day. Hubby often wants to wing it; he just doesn't want to deal with the consequences of us not reading his mind and happening upon the thing he had in his mind but didn't want to communicate (b/c that would be "planning").
