1.) When I use the guide I'm getting a fail to parse for the reporting_attachment during the simulation. Per the JSON I'm setting up, it doesn't seem like this reporting_attachment is a valid setting. I can see the reporting section, but looks like a bug on the back end to me.
So I need to clarify something, after posting this I was able to successfully send an email when the watcher fired. The issue is with simulating the watcher firing. So it's looking like a bug within the simulation not the actual watcher.