When I removed the black spacer/nut I found the source of the leak. A few holes. I picked up a new SP1408, and have drained the pool down.
Do you think it may be possible to unscrew the existing hayward return in the wall leaving all the existing pvc, and then screw in the new SP1408? I imagine not since it's a scalloped hole and I'd need to flex the pipe toward the hole by 1/2-3/4".
In your second example, assuming I can flex everything enough to get the coupling in below the new 90, Do I glue both ends at once ... Then press and 1/4 turn both at the same time?