I did get a new/refurbished starter motor from Napa and installed it. Unfortunately I'm still having issues getting things going. I have included a youtube link below of various tests I ran.
I will say I backed the old starter motor off and the bendix spring was definitely not functioning correctly. When I backed it off I did a bench test and it did spin up like before, however I think the gear at the end had meshed with the flywheel and the whole motor was turning over including the fan (not trying to start, just mechanically moving). Which has lead me to believe the flywheel is ok as it did spin along with everything else just fine. I do think i must be facing a wiring issue here, i'm just not sure where else to look.