I will say this: we did get spotted dropping stuff from a sky bucket once. That's the reason I only did it once. When we got off a CM pulled us to the side, really chewed us out, drilled us about where our parents were, and told us we were supposed to be thrown out of the park. Scared the b-jeezus outta me. Doubtful they'd be so lenient in the current day/age. Even if the vicious kids with oblivious parents were an obstacle, I think it'd be a manageable one with proper warnings and adequate surveillance.
I imagine the evac procedure would be much more of an obstacle.
As much as I enjoyed the sky buckets when they were operational, I remember how long the lines were on busier days. It wasn't really a practical mode of transportation from point A to point B because if you had a rental stroller it wasn't going into the bucket with you. You'd have to walk back or get back in line on the flip side (can't remember if they allowed round trips without getting off and reentering...seems like they didn't). Either way, they weren't the most up-to-date looking things either. They fit nice enough in Fantasyland but quite odd in Tomorrowland.
I'd love to see something done with the stations. Fantasyland's would make a neat restaurant, retail, or indoor character meet-n-greet. Tomorrowland's could be turned into the same thing.