I just transitioned from Itunes 08 (PC) to iTunes 09 (Mac). Can anyone tell me if iTunes 09 now does automatic updating of the library if I have my files stored in my own directory and structre and I then add new songs? If not, do I just need to drag them into the library after dragging them onto my iPod each time (creating a pointer back to my folder - using option-click or something of that nature)?

Lastly...I don't want to go there but if I make the move to let iTunes 09 manage my files instead of using my own folder structure...will it then allow automatic updating as I add files to my ipod/library?

Thanks for any help you can offer!