Upload and Attach local file (.pdf, .doc, etc.) to Admin>Tools>Send Email?

I've searched throughout the forums and the only thing I've seen close is to have a general .pdf file or other loaded onto the server. For each order I have, I send out a custom confirmation email from the Admin>Tools>send email. Basically copy and paste html code from whichever template (activity tour voucher) I need and type in the appropriate info.

As I'm bringing another person on to help, I'd like to just be able to quickly add info to a .pdf and upload and attach to the message.

Any ideas? In a few months, I'll look for a custom mod to dynamically generate the .pdf but until then this would be the easiest way.

Many thanks in advance for anyone taking the time to answer. Always a great community here..