<VV> Broken bell housing & flex plate

[Joel McGregor]

I'm working on a '66 110 auto with only 37k.  The bell housing broke as well as the flex plate.  No idea which came first but I'm thinking the bell housing.
With it apart I noticed a lot of wear on the end of the crank where the 3 bumps on the converter touch it around the pilot hole.  It has 6 worn spots so it must have failed before and then when the converter was bolted back on it was in a different location.
I've got records going back to around 1970 so it must have happened before that.
My concern is that it will just do it again in a few thousand miles.
Any ideas on what to look for?
The pilot hole in the crank is a little loose.  I'm thinking some brass shim material to take up the slop.  I've got some that's about like paper.
Thanks!
Joel McGregor