Ok, after much headache we've identified the bugs causing Ben's issues in the GML. Much thanks goes to Ben and the GML for their patience as we tried to figure this one out. They were introduced in 1.8.1 when I split admin email settings off of the regular email settings and moved a lot of the DB queries ahead of sending email.
1) Draft Admins changing draft options cause email settings to turn completely off.
2) If no mock draft was run then email is never sent and teams do not go on-the-clock properly. pick_time and pick_start are not populated. And an admin has to start/stop the draft after every pick to set them
I've created a patch that addresses these issues, and posted it on the main page. 1.8.7.. yep, we killed those bugs. RNFL, DFL, if you're listening, you're already running this update.