On the issue of required planning at DLR vs WDW, yes WDW takes more planning. But do not let that stop you!
Folks get so zoned in on their comfort zone. DLR? Yes, last minute, seat-of-the-pants can and usually work great. MP and legacy FP which you can get the same day is nice. Lots of dining options. Etc.
WDW takes more planning. But, there are lots of really good resources for that. Way more than DLR. I mean, for DLR planning, many of us just use this forum here. That is all you need. And just about all there is except for some other online forums.
The WDW forum here on DIS is by far the best on the internet. There are guidebooks (if you like those) and numerous specialty websites to help.
Plus WDW, as a resort, just offers more things to do than DLR. The space they have is awesome. Heck, almost all of DLR (parks/DTD/hotels) could just about fit inside the Epcot or Animal Kingdom parks.
Yes, you need learn some new things about
MDE online and app, Magic Bands (which are pretty cool BTW) and FP+ (different than DLR, but it works). Lots of really good DIS threads on how to do FP+.
There is a ton of magic out at WDW in ways you would never think about at DLR because DLR really is not set up to provide it.
