OK I got something up and running!
You should now be able to download the contents of that folder and double click on the PDR18 Boundary Overlay project and see what I did. Don't bother watching the FCP video, I only used a small section to overlay boundaries on in blue using PD18.
For your projects, you'd want to take a screenshot of the view you want to mark, then use a free app like GIMP or Paint.net to create lines or the full shape with a transparent background. Use individual lines if your clip has a low flying drone like at the end, or a full shape if the view is mostly from farther away.
Then place the overlay on a lower track so it appears "on top of" your clip. What I did was to align the overlay at the start and place keyframes for Scale, Position, Rotation and Freeform and then go to the end and adjust the image as needed to line up. PD will automatically place ketframes for any setting that gets changed and will automatically interpolate the changes in between.
If the motion is smooth across the clip, that's all you should need to do, but if there are any speed or direction changes (and there are speed changes in both of these shots) you'll have to add more keyframes where the changes occur and/or at the midpoint so that the boundary lines will more closely track the parcel.
As I mentioned in the linked post, you may notice some jiggling when the blue lines are drawn over the white ones, but those kinds of imperfections are much less noticeable if your lines are the only ones on the screen.