Robert, I had a similar problem with my TR in the past. It is at least on the TR6 not uncommon for the ring gear to back off the fly wheel. When this happens the starter will chip off the front of the teeth on the leading edge. It will then develop 'flat spots' until it's completely unable to engage the ring gear. You can tell by removing the Starter and looking for a gap between the ring gear and the front (engine side) of the fly wheel. The ring gear should be flush against the leading edge of the fly wheel. It's been my experience that once the ring starts moving backwards it's only a matter of time before you are unable to engage the starter.
Good luck,
Roger