(Apologies if there is a good existing topic on this - I searched but couldn't find one specifically about managing USB drive music files.) I'm curious how people - especially those who've used or migrated from iTunes - manage music files on a USB drive? How do you "sync" the drive with new music or otherwise update/remove files? I'm going to be taking delivery of a CPO Model S next week. I'm really excited and looking forward to it but as many know the media abilities are a "bought it despite this" thing. I am a music nut and have a huge library; I'm currently using an iPod Classic 160GB with a 10 year old Alpine head unit, which works really nicely for being able to control and find music among the 18K tracks I have on the Classic. Obviously, I'll have to migrate that to a USB drive for now. At some point I might bite the bullet on a bigger audio upgrade to incorporate a hi res player or something but for the near-medium future, USB is it. I picked up a decent and large (256GB) USB drive on sale last month to use. So I have all of my music in a couple of iTunes libraries, one as Apple Lossless format (which is where I rip CDs or download hi res tracks) and then a 192Kbps library that I down res to for syncing to the iPod Classic. I've tried copying files from iTunes to the USB drive, but man it's a pain just to do the initial copy and for future "syncing" I'm not sure of the best way. Should I just do a straight copy of files? What about actually creating a new iTunes library on the USB drive?