If you love your Apple iPhone / iPod, the latest release of Ubuntu from Canonical called Karmic Koala ( the counter part to Microsoft’s Windows 7) is totally compatible for USB connection.
Ubuntu uses Rhythmbox for playing songs and uses FSpot and Gimp for images. The audio quality is excellent ( even if you are using very old hardware like I do) and Gimp is the best image manipulation software -comparable to ones from Adobe- intuitive and easy.
DECISION STATS 
Rhythmbox is very good, but Amarok is just too good.