Motorcycle Repair: Ringgear/starter, heritage softail, jackshaft

Question
I have a 1998 Heritage softail. I have replaced the ring gear and starter 3 times. The starter does not engage properly and destroys the ring gear. The bike only has 23,000m. Any help

Answer
First thing that comes to mind is the timing is way off. to far advanced and the starter gear slams into the ring gear and will start chipping the teeth.
The other thing to check is the bearing in the primary cover. If the jackshaft is to loose in it the teeth dont mesh properly
Good luck and happy riding
Mike