I can also confirm this bug, on Feisty (Rhythmbox 0.10) as well was with
the current SVN version of Rhythmbox.

As Ben Hall mentions, an (annoying) workaround is to create a
.Trash-$USER folder in the root of the mount location of the ipod. Then,
Move to Trash will move the file to this location after removing it from
the ipod database. Now, you are free to remove the files manually from
this folder to actually free up the space (Empty trash in Nautilus
doesn't work for me).

I believe this bug stems from the fact that the ipod plugin
impl_move_to_trash (rb-ipod-source.c) uses rhythmdb_entry_move_to_trash
(rhythmdb.c) to remove the file. In rhythmdb_entry_move_to_trash, if no
trash exists for the volume (ie trash == NULL) the function will return
without doing anything.

See the related Rhythmbox bug thread:
http://bugzilla.gnome.org/show_bug.cgi?id=346434

There is a patch there which modifies the behavior so that when the
trash cannot be created on the ipod, it instead unlinks the file (with a
confirmation dialog).

-- 
[feisty] deleting a song from the ipod only updates the database
https://bugs.launchpad.net/bugs/96669
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