So I tried a test in photoshop with pictures and it was super easy, and I thought looked decent.
On the pool shot, I took a sharpie over my screen (over plastic) and lined up the swimming pool lines and then lined up the pool table shot. Everything is a static shot since I didn't want to have to do any crazy tracking.
I thought I'd give it a try with video in AE, but CC Power Pin is making it difficult to get the perspective to match. When I mask it, the pins move way off the corner of the screen and seem to be very finicky. In a way, I want to lock exactly where one corner pin is, but when I try to move another one, it just shifts it off and makes it unaligned.
Would this work better if I sent it to mocha? Is that even necessary? Can I reset the pins after I do my mask?