I actually think that block is a very pretty entry way to WDW. All the mature trees, flowers, plants, and lawns and the meandering road make it seem like you are driving through a park. As a result, many of the buildings are covered by the trees and not so easily visible from the road. The Holiday Inn, Best Western, and Wyndham are the worst looking in my opinion but you can hardly see them. I actually like the signs for the hotels. It is nice that they are cohesive and all match. They blend into the landscape and look a lot nicer than the ones for hotels outside Disneyland.
However the interiors are all updated and I am sure that most guests would rather have an updated room on the inside rather than an updated hotel exterior. Save the money for an exterior renovation and reallocate it towards new guests amenities. If the hotel companies really felt that their brand was being compromised by the appearances, I am sure they would have updated the exterior. But it probably isn't that big of a deal.
I actually kind of like that they have keep most of them the same. It is very old school Disney World as most were built in the early-mid 70s. It is a reminder of how things used to be at Disney World and the original design aesthetic. If every building was torn down because it looked old compared to current trends, the world would constantly be under construction. It's not that big of an issue in my opinion. When I drive through, I'm thinking about how excited I am to actually be at WDW. Disney probably doesn't want those hotels upstaging their own resorts.