I replaced my headlight motor with a brand new headlight motor around October and these motors are the unscrew and open case kind, no glue required to seal. I put in the metal gear expecting a lastable gear. I was horribly wrong. It lasted 1 month and the grinding returned. then I rotated 180 degrees hoping it would last, it did... ...for 2 more days...and the grinding returned... Im at a loss for thoughts...why is my headlight eating gears like this? This is ONLY happening on the Driverside

 

Sounds like the motor you put in has an issue/defect.

 

Now it appears the passenger side has stripped aswell! I am extremely fustrated... How can I fix this once and for all?

 

Just a wild guess, but I wonder if the headlight door module is not responding to the fact the headlight doors have hit the "stop" and the motors need to be turned off? See if you can find a module in a junk yard.