Quick update for those who may have similar issues are running through process of elimination for all possible errors.
I just got a call from the guy who rebuilt my starter. He said it was all done correctly, except, he added a washer in to the bottom of the shaft that did not require a washer. From what I've seen online, this is one of the ways people "shim" their starter, from the inside. Apparently, he said he rebuilt about 4 that day and may have gotten a couple mixed up. He said the washer is about 2 mm, which he said appears to be where the starter is wearing. When I looked at the fly wheel, it does look to be just slightly nicking the edge of the flywheel, so that would do it.
I'll get it in the boat just to be sure, but this (hopefully) sounds like the problem.
So, just to recap here.
If you're having these issues, get your meter out and check your slave solenoid that feeds the starter solenoid. Make sure it isn't sticking open or closed. Mine actually stuck closed at first, and then eventually open. It was an easy change for me on my boat. The part cost $34 with tax at a Marine store near Melbourne, FL.
My starter definitely needed to be rebuilt anyway, but as you can see, there is certainly a chance it's purely mechanical over electrical. The Starter rebuild cost $125.
I'll report back when I'm floatin' and boatin'. If I come back completely dejected, you'll know why.