This is failure to comprehend the user story underlying the use of email in OP's example. You're assuming an email always needs to be sent, and that as a consequence any transfer mechanism outside of email represents additional steps. OP's user was using email as a way of maintaining a record of when files were distributed. Email is not the only, nor best, way to accomplish that. There are plenty of file management and version control systems out there which can handle arbitrarily large files, and which would not require the sending of an email. Drag file into UI, tag appropriately and @ the recipient(s), done.