Adding some messages to “Waiting for reply” folder

My use case is that I want to track for responses on some messages I write. My methodology now is to wait for the message to be sent the move it from the sent folder to the "Waiting for reply" folder which I go over periodically. 

I'm looking for a way to automate this. Best would be if I press a key which makes Outlook both send the message and put it in the Waiting folder. E.g., by using an applescript.

Alternatively, I thought that pressing a key will add me as BCC, and also add a "*WF*" string at the bottom of the message. Again, with applescript. Then when I send the message it will also arrive at my Inbox where I'll have a rule to move messages to "Waiting" if they contain "*WF*"