To close the loop (somewhat) on this issue, the issue seems to be stemming from the setting "Leading Angle" on the boring bar tool. Setting it to a value less than 10 degrees is needed. I quickly sketched the insert in CAD to double check my "napkin math" and it appears a value of 5-7 degrees should be required, based on the insert definition. Setting it to one of those values allowed the toolpath to simulate with no issue.
Now, it does appear that there may be an issue with Fusion, since this should technically be possible to do even with improper values. We are looking into that issue
Seth Madore
Customer Advocacy Manager - Manufacturing