Rules module doesn't send emails to user roles once conditions are met
Attempt to answer this part of your question:
Any insight to why rules isn't generating emails would be helpful.
I doubt that Rules is the culprit ... and that it is rather something in actually sending the eMails. To verify this, just add a Rules Action to "Show a message" (as the very first Rules Action), and with actual content something similar to the subject / message body as what you have already in the Rules Action to send an eMail. Pretty sure that each time you'll get such extra message shown on your site. If it does indeed, you found a confirmation that there is nothing wrong with your rule itself.
However, just looking at the subject / message body of the eMail you want Rules to send: make sure to also verify that all those tokens (such as
node:field_announcement) are available (not blank).
PS: a completely different explanation might be related to your event "after saving content", whereas the saving actually happens ... "before saving content". To verify if that's what your issue is about, replace your Rules Action by an appropriate Rules Component (which does the same thing), and actually "schedule" that Rules Component (using the rules Scheduler) to run after just a few seconds or minutes (at that time, for sure the save will have been completed).