I can't see the finances ever working to support an expansion of the monorail, since the money spent could fund a number of attractions in all the parks, which would attract the crowds and bring in direct revenue. Nobody except for the real Disney fans are ever going to book a trip to Disney to see a new monorail line, but they would for new attractions/lands/parks.
However, I could see them making more of the monorail system as it stands. I have long thought that they could relocate the MK parking lot to just West of the MK (with paths/moving walkways/trams to the entrance). They could then turn the TTC and parking lot area into another monorail resort (which they could charge the earth for). This would also relieve the pressure on the monorail, since it wouldn't have to deal with day guests, and make it easier for everybody when the parks close. They could also put a resort on the STOLport site on the Epcot line.
However, I could see them making more of the monorail system as it stands. I have long thought that they could relocate the MK parking lot to just West of the MK (with paths/moving walkways/trams to the entrance). They could then turn the TTC and parking lot area into another monorail resort (which they could charge the earth for). This would also relieve the pressure on the monorail, since it wouldn't have to deal with day guests, and make it easier for everybody when the parks close. They could also put a resort on the STOLport site on the Epcot line.