The Matterhorn will probably stay, due to popularity, but they did consider tearing down the whole mountain and starting over given the conditio some of it was in, (rotted wood). It's just a relatively thin layer of concrete over mesh, wouldn't be that hard to take down despite the fact it looks like an immovable mountain.
Pixar's Inside Out will feature a "train of thought" that travels to "Imaginationland" which looks like Fantasyland, and Dream Production, as well as other "areas". Lasseter visited the Imagination Pavilion to take a look at the ride that is there, can't help but think that an Inside Out makeover would make sense.
Roger Rabbit . . . that film came out a while ago, and they didn't follow up with sequels, and the fan base probably isn't a tenth of what the princess fanbase is, or the fans of the newer Pixar/WDA films. I'm kinda thinking that it, and other areas of Toontown are kinda ripe for redevelopment.