I feel your pain. Especially about the bookmarks. I haven't tried Canola2 yet so I can't speak to that. The closest on I have found was podsync (which is actually a GUI front end to bashpodder for Maemo).

It will create dated playlists for Media Player, and when your done with a playlist (IIRC) you can delete the playlist and the files will go along with it. I could be wrong about that last part though.