I think if we took it one step further you could develop custom workflow templates with assignments and a custom message.  Instead of doing it on the fly you can apply the workflow template to the proof.

In an existing workflow you can click the 3 dots next to a user in the workflow, next select message.  This allows you to message an individual user on a proofing workflow.    You can add a custom message to a new stage

You are not wrong, when we switched to New Home I had to login as people, and manually drag the widgets around for about 3 dozen people

Layout Templates used to be able to toggle whether the Proofing icon displays in the main menu or not but I don't see it in my layout templates anymore.  I have no idea what controls the Proofing icon now.

Is it possible that email related technology infrastructure on your side is causing the delays?  How can you be certain that it is Workfront?

We have noticed this issue in our environment as well

We noticed the same issue starting last week.  Adobe seemed aware of the issue when I spoke with them on the phone yesterday so it's strange not to see it on the known issues page. Our workaround is to click Documents -> Document Details Then click the 3 dots when viewing Document Details - select m...

I realize that you might have already found this solution, but renaming the files to the desired name just prior to upload seems like it would work?

I also use "last note text" as a column in a project report to pull in data

@RowvillBh1 I don't see them in my environment either.  Comments used to be visible in the Update stream and each proof comment was prefaced with "Proof comment:"  I am unable to see comments in project update streams now, I think that something may have changed with that recently.