Does it work this way if you have two (2) iTunes libraries on one (1) iMac? No, is the answer in my experience.
No, is the answer in my experience. Upgrading my iMac to Mavericks made a hash of two iTunes libraries, esp. the books in each. So I rolled it back to Snow Leopard and restored from Time Machine.
iMac, Mac OS X (10.6.8)
