I have finally gotten my old Mac HDD sorted out, and now I would like to know if anybody has either: a) a way to run iTunes without wine, as it did not work out well for me the last time I tried it, or b) any other media player that will sync with an iPod and, more importantly, use the same file system.

When my Mac died, I started to get into open source. I bought a MacBook Air, only out of necessity. For almost two years now, I have not once backed up or synced my iPod. I am getting nervous that it may give up on it's life soon and would like to find a solution. I don't have enough room on my Air, and it would just erase my iPod anyway...

Another thing that I am having trouble with is the way iTunes arranged the music. Now, it is arranged all by artist, then album, the song and I would like to have a media library, but somewhere around 400GB of music is a lot to sift through (I have attempted in the past). Thus I am looking for something that will use the same library format.

A side note: As I was writing this I started to wonder; Is a Hackintosh in order here? If somebody will give me instructions on how to install MacOSX for free (maybe Mavericks?) in a dual boot with Ubuntu, I will be ever grateful. :)

Thanks, soundblastdj