I've uploaded a screenshot showing my macro, which works great for one attachment. I'm trying to figure out how to attach two files to an email. Does anyone know how to do this?
"To attach a file click the File Chooser button to the right of the action to select an existing file on disk. Option-click on the File Chooser button to show the currently selected file in the Finder (assuming it exists already). You can only attach a single file (if you need more than one file, it can be done with AppleScript)."
After you've attached one attachment with the KM action you could others by driving Mail with KM actions -- ⇧⌘A to add an attachment, ⇧⌘G to open the path dialog, etc (plenty of recent threads on how to drive the Open/Save dialog).
AppleScripting an already created outgoing message can get a bit... interesting since the ability to reference frontmost outgoing message was removed from Mail. So I'd skip the KM action and AppleScript the whole "new outgoing email" process -- shout if you want an example.