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Help: Need "SEND EMAIL" button on QUOTE detail page that attaches the attachment from "Notes & Attachment" section

 I need the ability to send an email from a quote detail page that automatically attaches the file (only one file) under "Notes&Attachment" section.
So there are two ways I envision this: 
1) A button that sends email (gets address from "Email" field under Quote detail page) and attaches the file
2) A button that opens up the standard email page with the attachment already attached and I can lookup the contact and write the message and send an email

I have no idea which is easier and what are the steps to accomplish this, so any guidance is appreciated.