I’m not sure about auto-raising invoices and saving to pdf from within GnuCash, 
but certainly, you could do that automated outside of GnuCash.

I would think with a Calc sheet or Base file to handle who gets what discounts 
as well as holding the customer info, you could use a macro or script to 
generate the invoices and export them to PDF. The macro/script could then 
fill-in the pdf filename and location into the Calc sheet/Base table that is 
then used to generate the e-mails with proper attachments. The generated 
invoice data should also be saved to a csv file, you can import them from the 
csv file into GnuCash for your records. You can have one csv per batch if you 
like, no need for one per invoice. (note, there is a favored data order format 
for importing csv invoices - check the list archives and wiki)

Just be careful about sending out batches of e-mails. Most ISPs as an anti-spam 
measure have an hourly and daily limit. I suspect sending 80 all at once would 
trigger it for the hourly limit. (of course spammers get around this)

You can manually hit ‘send’ in small batches, or use a mailing service or 
software that sends them over a short period of time for you. I suppose if 
you’re scripting all of this anyway, the script could put in a 60 second or so 
pause in between each one.

You could probably reduce this work to a minute or so of clicking.

Regards,
Adrien

> On Jan 31, 2018, at 1:59 AM, bob_summers <[email protected]> wrote:
> 
> Hi, I've been using GnuCash for a few years in my business, a language
> academy, and it does everything I need it to, which is; generate invoices,
> track their payment, and send a few reports every tax quarter.  I send
> around 80 invoices on the first of the month, generally all for the same
> amount (some get family discounts).
> 
> My current workflow is:
> 1. Raise 80 invoices, 
> 2. Generate easy-invoice reports for each,
> 3. Save these reports to .pdf
> 4. Mail out the reports (Thunderbird).
> 
> All of this is done one by one, takes a few hours, and is prone to errors. 
> If anyone has an idea how to automate any of the steps, especially the last
> three, I'd love to hear about it.    
> 
> Cheers!
> 
> 
> 
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