I am on my second Stiletto since June as a result of the same issue.
I have a 8GB memory card in my Stiletto and most of my 1200 songs have transferred over from my Ipod to the Stiletto.
However, I can only have 1 playlist of about 75 songs. I have another playlist of about 20 songs. (I would like to have many new playlists but I keep being told that I have used 46% of my internal memory...and no new songs/playlists can be added.
I do not record shows (Howard etc) so I should have a full internal memory to run playlists.
Is anyone else having this problem or does anyone else have a suggestion on how to increase my playlists?