As someone who plans trips thoroughly I don’t think WDW was ever simple. It is definitely simpler to me now than it was when I was a kid and we’d have to buy travel guides, maps, call hotels, tourism bureaus etc just to find out what was even possible. It would take months to plan. I’ve spent the last few nights planning a trip to Syracuse and Rochester so I never make travel “simple”.
My answer to the question would be working with youth.I work with kids in my area and we used to just say show up on this date and this time and a bunch of kids would show up. Now, they all have sports, music lessons and other activities that are up a greater percentage of their time and we have to really work to find times that the most kids can participate. Plus, we have to make sure we have the proper number of volunteers and that they all have their waivers. It’s much more complicated.