There are many people that see the TV ad, and then start planning their trip. It is amazing, but if you ever see their TV ads, they are geared for people that would be making reservations and traveling in the next couple months. Look at the fine print the next time one is on.
So, please do not get me wrong. We have been DVC & AP holders for quite a while. I have easily spent over a year of my 47 year old life on vacation in Orlando, mostly at Disney. IMHO, you have to have a plan to enjoy it.
However, to the causal (or even worldly) traveler, who would think how much planning is needed? With 36 resorts providing over 30,000 rooms, and tens of thousands of more rooms provided off-site by hotels, timeshare, home rentals, etc. who would think getting room would be difficult.
By my count, there are about 285 restaurants on property (everything from a pool bar to an ice cream shop, to the bakery on main street). Who would think that you could not get a reservation at one of the 100 or so sit down restaurants (estimated from the 100 restaurants that accept Tables in wonderland).
So, yes, we plan our trips like they are going out of style. We do everything in our power to lower our wait times (arrive at rope drop, carefully schedule FP+, etc.) We also do everything in our power to save money while there (DVC, AP, TIWL, etc.) We also do what we can on our way in and out. For example, we live 8 hours away by car. Depending on the trip, often we will leave after work/school and drive to about 2 hours outside Disney, then stop for the night, often staying a hotel cheaper than it would be in Orlando, or on points (again less points than Orlando). Depending on our vacation, we may also do a similar return trip, staying in the parks most of the day, and leaving after dinner.
One of my perks at work is sometimes we get a recognition, and one of the things I can get for my recognition are gift cards to Landry Restaurants (Rainforest Café and T-REX). Again, a free meal.
As many people have said, no place else on the planet requires this level of detail. I had a trip to Las Vegas last month that all came up within 2 weeks. My co-workers and I had no issues finding a place to eat, seeing the various sites, etc. And while much had changed in the 10 years since I had last been there, so much was also the same.
Sadly, we have had friends and family that have booked and went to WDW without ever talking to us. Then all we hear is “How can you like it there? One day we only we did 4 rides! Great Adventure is better.” Attempting to explain that planning a trip and arriving on December 27th, then sleeping in each morning and getting to the parks by lunch time, was like talking to a wall.