For #2, Rhidian's code should work if you register that trigger for both players and items (two separate functions).
I think #3 could work if you had a character with a set path. You'd have to set the tracking markers on the path of the character manually and then set them offstage. When you use the ability on the character, you'd put the markers you placed on stage.
If the character doesn't have a set path (e.g., is on a wander script), then I have no idea how you'd do it.