Hi @JustinArndt!
I noticed your post is a little old now, did you ever find a solution to this?
Square probably isn't the sole platform you'd need for something like this.
If it was me, I'd be looking at maybe using something like Microsoft 365 Power Automate (ie setting up a flow that is triggered when the customer's invoice is marked as paid, automatically send the report (which could be in a folder on your OneDrive by itself, and the rule is that it's attached to and email)).
For example, we're a very small barbershop in Brisbane, and I love automation (keeps our costs down!), so I've got a flow setup to automatically send our bills / receipts to Xero. It doesn't require any code or programming. There are thousands of pre-made flows that are easy to start with. For us, essentially one of our best flows monitors our Outlook email account and auto-file anything with 'invoice' or 'receipt' in the subject or body to an email folder, then PDF it, save it to an expenses folder in OneDrive, and then a separate flow detects any new files in that OneDrive folder, creates an email to our Xero bills address and sends it in ready for us to approve it and then reconcile against the bank feed. The same applies when we scan physical receipts on our Epson printer (I have a shortcut setup within the Epson app that saves the scanned PDF to the same OneDrive folder), it's then also auto sent to Xero. Super simple automation that saves us hours and hours every month getting receipts into Xero (time is money to me!). This is just an example of how we use it for something pretty simple, and it could be a similar formula for you except you'd be wanting to connect Square or Xero and your trigger would be once the invoice is marked as 'Paid' is when the flow runs essentially, but the file in a OneDrive folder steps would be the same.
Microsoft 365 subscriptions start at around $18 per month for the full kit, which includes Power Automate, and this to our small business is a justified cost based on having reliable and capable enterprise grade email, OneDrive (our whole business is setup in OneDrive, nothing is on paper), and the benefits of the rest of Microsoft's online ecosystem like Power Automate, OneNote, Word, Excel etc. This costs nothing in the bigger picture of the time it saves us just on the automation alone! Personally I'd love to see some more integration between Square + 365 (calendar would be a great start) but that's a topic for another day.
Xero may also have an option to do this too as part of its invoicing functionality (ie you could add it as an attachment to an invoice etc, but wouldn't work for someone you're waiting for payment from first).
Hope that gives you some ideas if you're still looking. If you need some more help, feel free to reach out, I can help you try the Flow option based on the above.
