Hi,
What you could do is use the PDF invoice plugin:
www.hikashop.com/marketplace/product/18-plugin-pdf.html
With it, you can select the orders you want in the orders listing of the backend, click on the "invoice" button there, and it will give you a PDF file with the invoice of all the orders you selected.
Then, you can send them that PDF.
Now if you want to automate that, it would require the development of a plugin, potentially basing yourself on the PDF invoice plugin, but not necessarily based on what you want precisely.