Flywheel/starter not meshing

I just had to replace the ring gear on my 66, 289 4 speed.  Ground or broke the teeth off of the gear.  The starter would catch 75-80% of the time and spin like it was grinding teeth again after replacement.  Tonight on the way home from a cruise the car stalled and would not catch to start.  Seems like I am right back where I started.  What am I not doing right.  Tried to shim the starter with minimal success.
Bob Hamilton  

Did you replace the starter also? When I quit using rebuilt starters was when I quit having flywheel ring issues. The bendix gear on rebuilt starters is reground, not new and I believe don't line up properly and wear ring gears.

Also, I've yet to buy a new ring. It can be removed, turned over and replaced and you have a new side that's just like new. Flywheel is removed, placed in oven, flange side up because when the ring gets hot enough it will drop off. Turn flywheel over and drop on the ring, worn side the opposite way it was. I did this to my 66 in 1976, still works fine today. No rebuilt starters.  

Thanks I will try a new starter, 2 rebuilt ones and two ring gears.  Do you have a vibration isssue with the ring gear turned over?  I will try that first and maybe get a new gear when I get it to work.  Anyone had an issue with the bellhousing, seems to be the only connection between the two?

thanks for the advice
bob  

I didn't notice any change in balance by swapping the ring around. Ran it from 1976 until 1998. That motor I'm storing (original) and running a 347 stroker now. When the starter and ring gear started slipping, the ring gear teeth all around had their corners ground off. Turned the ring over and new starters since, when I pulled the motor in 1998 the ring teeth still looked good. 22 years trouble free  

there are 2 different nose lengths on those starters , a long nose for the factory auto flexplate and 157 tooth manual flywheel and a short nose for the factory 164 tooth manual flywheel , when you buy a starter take your old one to match it up,jeff  

(brain fart).  

Seems to be that whoever built the engine before I got it put on a flywheel for an automatic.  Measured the offset from the flex plate to the ring gear, matched up to starter for an automatic.  Amazing what a half an inch is in tight tollerances.  Car starts every time, like it is supposed to.

Thanks for all the input.
bob  

Great you've fixed it. Your last statement confuses me; did the car come with a flex plate and a manual trans (unlikely) or did the PO have a automatic starter on a manual bell-housing? jlgcc  

the car had a manual trans, starter for a manual trans that would not engage.  I didn't check the part # when I had it apart to replace ring gear.  Installed new starter for a manual and chewed it up in a week.  Checked the offset and it appears it has a flywheel from an automatic.  Had an auto and manual starter side by side and the auto is about a half an inch longer.  Manual starter would engage 75% of hte time and not work/chew its teeth the rest until it had no more gear.  Not sure but it works every time I turn the key.  Now just waiting for the rain to stop to enjoy it.

bob  

ok im glad i found this post, i have a 93 mustang with a 5.0 doing the same thing. i put the motor in about 2 years ago and have probably replaced the starter 12 times since, ive baught new and rebuilt, different brands and year models. replaced all the wires, mine has a slight differance how ever. ile put a starter on and it starts it every time for 3-4 weeks just fine. then it starts engaging or disengaging ruffly. shortly after it quits engaging the flywheel all together. ive got the standar T5 tranny as well. ive checked the fly wheel multiple times and even had it machined. there are 3 slightly warn teeth on it but thats it. however the starters still just get to the point where they no longer kick out to the fly wheel. could i have the same problem as what is posted above and have an somthing wrong or does my car just hate me?