This could work with some major infrastructure reworking.
So I had to do some slicing and rotating to get it to fit micechat's attachment specs, but I think it's still understandable. Infrastructure rebuild as follows:
1. Remove the green structures.
2. Build a new building in the green space the size of the yellow building likely with a lot of underground work to make this building large enough to hold as much of the backstage as possible. In order to preserve sight lines, Toontown may need a larger "mountain" range facade.
3. Once the new yellow sized green building is built, remove the brown and blue structures, which could now have their contents located in the new green building.
4. Move the pink Corral to the brown space and remove or rework the orange structures to also fit.
5. Remove the red structures.
6. Build a new structure in the red zone large enough to also contain the purple buildings. Sight line facade on the back of the New Orleans train station may be necessary.
7. Remove purple structures.
Now you have a clear line to go around the berm and connect Critter Country to Toontown with room for three or four rides and tons of shops and scenery. You are already under and outside the railroad, no tunnels or bridges required. If you want to link Frontierland over the railroad with a bridge, it's pretty easy. All said, multiple warehouse builds and movement with a total cost likely in the range of 200 to 300 million, opening up huge tracts of land for expansion.
I've long been an advocate of the theory that Winnie the Pooh gets short shafted as a bad unpopular dark ride merely because of it's awful traffic flow situation. Yes, the Big Thunder Trail empty path phenomenon is possible, but I find it more likely that if you build new attractions around the outer rim outside the berm that not only would it be a well traveled line, but Big Thunder Trail would also see increased traffic.