I pulled it apart tonight and think I've solved my problem. I stretched out the spring and added another washer to give it more force on the back of the drop target. IMG_2597 (resized).JPG
But there's really not much for the target ot sit on. The "ledge" that the target rests on is a wafer thin piece of plastic with a slight bend in the middle. IMG_2598 (resized).JPG
The apex of the bend just so happens to be in the same spot as the cut out on the drop target. IMG_2601 (resized).JPG
I'm sure this has been rigorously tested but it just seems flimsy to me. (But I'm not a pinball engineer) here's another shot from the top of the Playfield, you can see how thin the plastic strip is.IMG_2600 (resized).JPG
So far the drop target has worked 100% since I put it back together, but if I notice more issues I'll post it here.
Let me know if you think there's a better way to solve this problem.