Thanks for responding lowlander. I saw this reported also as a bug at:
http://www.ventismedia.com/mantis/view.php?id=6343

It is currently very painful trying to sync playlists to devices that don't support m3u playlists. This would be a very useful feature in this case, and seems like it would be trivial to implement. Is there any chance that this would get added as a feature in future versions?

No, unless you use the manual Send To probably.

I just ran in to this same issue. Does anyone know how to do this?

Another reason the Folder (Rip/Convert) option isn't ideal is it converts EVERY track. I have both FLAC and MP3 files in my library, but the playback device doesn't support FLAC. So I just want FLAC files converted before they're copied. Auto-Sync lets me specify compatible formats for the device and it will only convert incompatible tracks.

I'm trying to Auto-Sync a bunch of playlists to a USB drive. The music will be used on a device which does not support m3u playlists. In Device Configuration I setup the destination directory structure to be \Music\<Playlist>\<Title> so I can play my "playlist" by playing songs in a directory. However, if a song is in more than one playlist it only exists in one playlist directory.

Is there a way to have Auto-Sync allow a song to be copied over twice if the destination path is unique?

I know I can right click over a playlist and select "Send To -> Folder (Rip/Convert) -> Folder Path" and it will do duplicates, but I have to do this for each and every playlist I want to include (and there are a bunch) and I have to create the playlist folders as I go. It's much easier to just use auto-sync and have MM do its magic.