are you using a regular Chrysler starter or a light weight starter?
alright, you said your using a Lakewood bell. now, what size flywheel? 11" or 10.5"
the Lakewood bells have to be set up for 11" or 10.5" out of the box. depending on the flywheel your using, that will dictate
where the cup for the nose of the starter bolts to. also if you use the 10.5" (like i do), there's an adapter that holds the
starter in. so, there's not 2 bolts going through that starter and bell. one bolt goes through the starter and the other goes
through the adapter. there's a tab on the adapter that goes into the other starter bolt hole. believe it or not, that holds
the starter in with the 10.5" flywheel.
on to the transmission. the 23 spline trans has a smaller bearing retainer and throwout bearing compared to
the 18 spline trans. the hole in the bell for the bearing retainer is the larger of the two (18 spline). if you install the 23 spline
trans, there's an adapter ring that takes up the difference in the size of the bearing retainer.
now you have the 5 speed trans, what size is the bearing retainer? is there any gap between the bearing retainer and the
hole in the bell?
if something is mismatched that could be your problem. but why it was doing it with the auto trans too? ? ? ? that's weird
the other thing i'm interested in knowing is if the nose of the starter breaks off on the first start. or, does it take a while and eventually
break. when it does break, are the starter bolts still tight or did they loosen up. if they loosened, sounds like somethings vibrating
them loose.