Also please add the link to the idea on here when created so anyone who ends up here can vote on your idea to help get it delivered.
I created a similar Idea 1416 in June that is essentially the same issue. In every situation, the user has to manually press the 'Finalize' button to generate the PDF. And, to your point, output docs cannot currently be scheduled.
I have spoken with Professional Services and they have confirmed that there is no existing way to automate the generation of an output doc including service reports and service quotes. Instead, the solution recommended is to build the document in Visual Force and trigger the PDF and emailing if desired.