To add to what Steve's saying, perhaps there could be an option when attaching documents with DS that says "send with spec" or something to that effect. Since you might want to have some documents that DON'T print/email with the spec because they are internal.

I have a similar request from a client who wants additional documents sent with their Invoices when emailing the client. So it would be nice not to have to put a second copy (of the documents you just attached with DS) into the Additional Attachments folder and then have to browse to that folder on the spec printing dialogue for each invoice. Not to mention you can only select one document at a time for that function.