Thank you so much for the reply!
2) "You need to override the default page break code built into Order Printer." How would one do something like that? App development and api access?
Our final SOLUTION:
As float:left; does not work as expected we used our printers options to print four pages on a single sheet. Thus we made our html/css simply generate full size templates and we "shrink" those by our printers printing options. Et voila : )