Related Questions:
Can I generate a contract to include all the dates on a Recurring Booking?
Can I send a Document from multiple Bookings?
How can I send a document from more than one Booking?
Procedure:
As each of the recurring items is a different 'Booking' there needs to be a different Document for each one, however you can then link multiple Documents to your email to send them all at once.
To attach a Document from a different Booking into an Email:
From the second Document you are working on
Click Actions
Click Copy to Clipboard
Open up the email you are sending the first Document
In the email body, enter the visible wording you'd like for the Link
Highlight the wording
Click the Insert Link Button
Paste the URL
Click Insert
Complete your email & click Send