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What might be the problem? Raising the drivers headlight works intermittenly while other side works everytime. Repaired the drivers side with a brass gear in summer of 07 and things were fine. Now when the switch is turned on sometimes the drivers side will not work until It is turned on and off several times.
I had this same issue (as have many others) with my 1999 coupe. My driver's side would only work sometimes and gradually until not at all while the passenger side was fine the whole time. Even though I was not hearing any grinding noise I replaced the gear in each headlight motor but this did not fix the issue with my drivers side.
It was not until I replaced the control module (located behind the passenger headlight assembly) that my headlights began to work completely normally once again.
I bought a used one from a late model Vette from Gene (Karshop) here on the forum.