[jiggy2011]

I don't know if I'm just old school, but I prefer just to plug my devices in and drag files over. Seems fairly seemless to me.

[donniezazen]

I have thought about doing that but I would like to setup a media player which automatically generate playlist based on my listening habits like most played, recently played, etc. And it to work two ways.

Playlists can be very useful.

iSyncr and iTunes can do that but I haven't found a seamless solution for Linux yet.