Excellent additions to your symptoms ?
So when you said it's not either of those things, I think you were referring to not having the plug oriented wrong, nor cross threaded. Am I correct on that?
I have an older 21', so I don't have anything to do a direct comparison on, I'm going on similar issues I've noticed.
The cleanout plug tube is a rubber sleeve that connects to the bottom of the boat, and to the underside of the cleanout tray. The tube has clamps that keep the tube in place, and on my boat, if those clamps are too tight, it ovals the tube, and feels like the symptoms you describe, if it's happening at the base of the tube.
The cavitation points to the plug not being seated correctly, and would also explain the difficulty in getting the plug out, but it doesn't jive with it being easy to turn. That makes me think there's something wrong with the fitting that the plug screws into, or the plug itself having an issue.
Good clear pics, both close up, and from a slight distance, will be super helpful in trying to track down the issue, as well as video. Take a flashlight along to help with lighting, it may be better than relying on your phone's flash.
I'm also wondering if the tube may not be sealed properly, since you said this became evident after running the boat. I'm wondering if that turtle may have sliced the rubber tube with the shell, and the rubber is catching the tabs when the plug is turned. That would be a little more work to determine, but not too difficult to rectify if that turns out to be the issue.
Once this is solved, I think it'll address the other concerns you have, as this all sounds/seems related. You got this!