Yeah, it'll be a conversation starter, that's for sure.
And Disney knows this. They know people don't want to come to their park wearing a mask or standing 6 feet away from someone else while lining up for Splash Mountain..........................all the way down Main Street. They know this, and they are a business that wants you to come. Eventually this will pass and they'll want you to "Be Our Guest" again. It is very un-Disney to be like the outside world, and a mask will just remind people of the outside world. They don't want this. Like I said, how stupid does that look getting a picture with Mickey with your whole family wearing masks? It's idiotic.
My guess is they are in talks on a daily (hourly?) basis with the government in Florida. They want to open up but they know they have to "save face" a bit so that they don't look like they don't care. There is a fine balance. But in reality, no one wants to go to Disney World if they have to wear a mask before they enter. Nothing says buzzkill like that, and Disney prides itself in the atmosphere and the experience and the environment of their park. So maybe they'll wait until the panic dies down, and it is dying down gradually I have noticed.