I never do much printing, so don't really know any good tools for this.
I did some flyers for our second business (we get paper and laser printer toner for free, before the "Use a printing company!" comments).
I did the designs in GIMP and started to test the printing runs for our double sided flyers.
Windows' built-in tools are horribly under-powered for this. Photo Printing Wizard lays out the images well, 4 on a page, but when I started going for the bulk I was surprised to find a 15 copies limit - which meant I could only print 3 actual pages with 4 flyer images.
The normal Windows print dialog can do 4 per page, but then prints borders. When trying from GIMP it can't fathom why I would want to print 4 per page and just spits out 4 pages every time.
WTF?
I eventually just printed a 4-per-page to a PDF file and printed my large run from Foxit Reader.
Anyone know of any great print tools that can help if I need to do this again?