That's what I used -- well the LibreOffice version, anyway, along with the file system. An invoice was just a template that I filled out, and saved to a PDF. I didn't keep every invoice as individual pages, or anything like that. Then I put the PDF in a "pending" directory, moving it into a "paid" directory when I cashed the check.
If he's just going to do the occasional invoice, it's not that hard to use one of the built-in Word templates to write one up and attach it to an email. Much more than that and I think I'd go crazy with that system.
I only really had one client at a time.
I just ran across
these, after stumbling onto turnkeylinux.org with an unrelated search. Although running a VM just for invoicing is a bit overkill, it might be an option, if he's more comfortable with the idea of a web-based solution, but wants to keep it off the cloud.
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