Jim's ISP is attbi.com. I think they provide space to upload files.
He could upload the one file to the server.
Send out a message to all the iHub e-mail subscribers with the link to download. (ex: members.attbi.com/memberfiles/jimlurgio/file.pdf)
That solves it, eh?
While not as easy as attaching one file to one e-mail, it certainly beats the heck out of typing in, attaching, and pushing the send button 200-300 times as he has been doing.