I hope my question is simple and there is a simple answer. I bought an iPod Classic. It's either a 5th or 6th generation---I don't remember. I have "synced" over 1200 cd's to this thing twice only to lose them twice because I'm stupid. If you erase the songs off your lap top and have auto sync checked in iTunes it's bye bye or if you have an external hard drive and it's not connected and you have auto sync it's bye bye again. I now know how to use the thing now---I think---so I don't go through iPod hell again. Bottom line is I hate this thing. If I buy the newest 120 GB Zune will work just like all the other MP3 players I have owned where I just drop-and-drag and I'm good to go or has Microsoft programmed their own brand of hell in the Zune, too?