Im looking to make a mod to add more books into Skyrim, and am trying to figure out if there is a way to get them inserted into various locations (as a random chance, or otherwise) so that I wouldn't need to place every single one by hand. Anyone have any ideas?

You could add them into http://www.creationkit.com/Bethesda_Tutorial_Clutter#Leveled_Items lists. That would make it more likely to conflict with other mods, of course. Unless they've added in a way to do it via Papyrus. Haven't looked into that myself, though.

Im not paticularly good at Papyrus, so I likely couldn't make that work without learning it first anyway. Would using a new leveled item list and dummy books work any better? (assuming that I just did the work by hand)