Eh. I wear my New Balance tennis shoes almost exclusively - I buy ones for my foot type - and my feet are fine. Changing shoes is probably good if you're buying for style rather than support. I take a windbreaker and I'm good. In the unlikely event I get cold if there's one thing I can get at Disney it's clothes.
DME was great for my dad - he's 91 - for the luggage alone. Plus it's nice to get off the plane and realize you can leave the driving and navigating to someone else.
I'm the same with shoes. I have worked on my feet for over 30 years and I have to wear a supportive walking shoe. I have the one type that fits me perfect and supports my feet. I don't change my shoes out because it would just be the same shoe. I do change my socks out though. I agree that if you have to constantly change your shoes out throughout the day, then you are buying the wrong shoes.