Concerning strollers, I believe a large part of the problem is that Disney has changed its target market. It's gotten appreciably younger.
There once was a time when a Disney movie was fine for a 10 or 12 year old. Not anymore. Just imagine most 12 years olds watching
Finding Nemo or
Monsters U. Compare that to earlier decades when Disney brand movies included
20,000 Leagues Under the Sea,
Escape To Witch Mountain,
Something Wicked This Way Comes,
The Love Bug, or even
Mary Poppins. Disney aimed for an older crowd at a time when children were allowed to remain children longer.
I recall reading (not sure if it's true) that WDW originally was targeted more towards families with junior high children. Certainly, there was nothing childlike about EPCOT when it first opened in 1982. My recollection of WDW during the 1970s and 1980s is of a fairly small toddler crowd. It was mostly older children and their families. WDW then started targeting "adults only" in the late 1980s and 1990s. (DW and I spent our 1st Anniversary at WDW.
) It's only within the last 15 years or so that WDW started targeting a much younger crowd.
There are so many more strollers at WDW today in large part because WDW's visitors have gotten younger.