Update: Ended up seeing people talk about the grounds on this truck causing this problem to happen. Ended up checking the ground right behind the passenger side tire and it was caked with grease and dirt.(As seen in photo, if it works lol)
Cleaned up the whole area, sanded and wire brushed it all and put the screw back on with dielectric grease and some undercoating spray over it. Haven't had the problem come back again yet.
I just put some new tires and rims on so I had to remove the factory mud flap, as well as do a norcal mod and such, so that probably exposed the ground even more. Hopefully this will hold, otherwise I'll relocate the ground.