Found out what the problem was: Rear Wheel Bearings
They literally exploded. As in, they came out in pieces once the tire was taken off. The best part? Whoever changed the bearings before lost the spacer that goes in the wheel and replaced it with a cheap piece of pipe from a hardware store. Here's the kicker, the bike is AS-IS and Harley won't do shit to fix it unless I sell my first born child and both of my kidneys plus my left foot.
Seriously I'm pissed but luckily we ain't dead. A buddy is a mechanic and is fixing everything for free. So all I'm out of is parts. Best believe this POS is getting traded in soon