Thinking out loud about the Skyliner. I'm not sure Disney would ever take the Skyliner to DS as it would be an easier way for guests to avoid the park parking fees. Right now it's a pain to get from DS to a park as guests need to go to a resort first and transfer. This is time consuming to say the least. If the Skyliner linked to the parks (even via a resort) it might encourage guests to park at DS and hop the Skyliner to a park.
Another thought, I wish Disney would design a way for resort guests to more easily get from a park to/from DS. We were at WDW for 10 days last week and would have enjoyed more of the great DS dining options if it wasn't such a challenge to get back to a park from there. I wish they could design something similar to the after hours scanners where guests need to scan their MB before getting on a bus at DS that is going directly to a park. If you're a Disney Resort guest you may board a bus directly from DS to a park thus avoiding the trip to a resort only to transfer to another bus.
Stepping off my soap box...