iPod integration

[Klaus <klaus.doering999@gmail.com>]

Hello List

How do people here integrate their portable music player with their
Debian box? My daughter "inherited" a 2005-vintage iPod Shuffle, a
rather dumb device that holds one playlist, media files in a m4a
container, and it uses I believe mp3 encoding.

I've ripped all my CDs, to make them locally available on my headless
fileserver. The files are encode in flac, and are accessible through
either miniDLNA, a upnp server, or directly via NFS. The latter I use
to play the music via MPD (music player daemon), piped through a USB
digital-to-analog converter to my stereo (this is essentially a direct
replacement for my CD player), all controlled via Gnome Music Player
Client.

Now, my question is: how do I connect to my music with something like
Rhythmbox , VLC etc., to be able to compile a playlist, convert (on
the fly?) the flac files to mp3, and upload them onto the iPod?
Various bits of this process I can do, but haven't figured out a way
to do it all.

There are quite a few old recipes on the 'net, some involving
GNUpod. Is there anything new, more integrated?

Thanks in advance,

--
Klaus