63 Hawk pulling the flywheel.

[rkapteyn]

It has been mentioned here that the starter bolts are special.
You saying that one of these was bend indicates to me that you have the incorrect bolts.
The starter bolts are shoulder bolts to precisely locate the starter.
Not using these special bolts is probably the cause of the stripping the ring gear.

Google it!

Studebaker V8 starter bolts

Robert Kapteyn

[stude1964]

Savannahgreg
You might also want to check your pilot shaft bushing while all that stuff is out. Who knows who played with the car before? If you need a starter bolt I have a used one here in PA. I could send. As post #16 states they have a shoulder and fit snugly in the bellhousing.
Rob in PA.