Outlook Attachment Organization

My organization sends out daily emails with long lists of separate items submitted by each team member, with related documents corresponding to each individual item.  The current accessibility options for organizing attachments in either Outlook or Outlook (classic)--I use the latter--often make this somewhat of a challenge.  The protocol for sending these emails is not going to change within my organization, and I'm not in a position to suggest any kind of third-party subscription (e.g., NetDocuments) to help organize attachments or even to ask my team members to all download a plugin, regardless of the price.  So, I've come here to ask for help.

The default, of course, is for all documents included in an email to be held within an attachments pane above the message.  See Illustration 1.  This, however, does not lend itself well to the daily emails.  For instance, take Illustration 1 but instead of just seven attachments, imagine 30.  Now also imagine 10 items instead of 3, with lengthy paragraphs included in the {Summary} placeholders.  This may give you an idea of the issue I am trying to solve.

One workaround is to send messages in rich text format.  See Illustration 2.  This allows each of the documents to appear under the corresponding items and, overall, is much more efficient at organizing attachments for the task at hand.  However, the workaround presents several of its own issues.  First, my team is not an altogether tech-savvy bunch.  The thought of trying to get everyone to remember to send their daily email updates--and only these emails in particular--in rich text format is somewhat of a nonstarter.   Second, and more importantly, the appearance of the attachments using this method does not allow for the full document title to be displayed to the reader, which defeats the entire purpose of my endeavor:  to make it easy to identify and access documents corresponding to each item in a list without having to open multiple documents at once or sift through a sea of attachments to find the one you're looking for.

What I'm hoping for is something akin to what is shown in Illustrations 3a (above) and 3b (below).  (Note: I've prepared these illustrations by inserting screenshots of the attachment pane icons below the placeholder text.  Clearly, this is not something I've composed using existing features, otherwise I wouldn't be posting this query.)  Ideally, one would have the option to choose between a layout akin to either Illustration 3a or Illustration 3b.

Thank you!