Your mention of shearing teeth reminds me of my 66 Rambler Ambassador.
That car needed some dental work on the flywheel and sometimes screeched when I tried to start it. Each "screech" would move the flywheel a little bit and the starter would eventually grab enough good teeth to start. 2 - 3 screeches at most. ;-)
But what I was really reminded of was the "switch" I installed for the sound system. The AM radio in a 66 Rambler Ambassador was not the type that could be replaced with an aftermarket AM/FM radio because of the vertical mounting layout of the factory radio. Tall and shallow vs. short and deep like most radios.