Definitive Milestone Email Notification Configuration

Currently we're on 9.1 through bund #23. I'm  trying to get the Grants Milestone email notification to work using the Role based workflow.  I've reviewed multiple documents (includeing HEUG presentations, service request docuemtation) and I'm missing something in the configuration somewhere  and can't figure out what.   I have two roles setup for workflow - CNT and GA , with both the milestone and professional options checked.  Our setid is UMASS - we have deleted all the SHARE Setid values in favor of our UMASS setid.. 

I have two versions currently setup  - one works, one does not.

First award t - I've only setup contacts on the Milestone contact page associated with the Award. I can send the emails via the notify processes. But htat means on each milestone setup, I have to add the contact. With multiple milestones per award, that makes this a bit redundant and heavily maintained.