Automatically delete songs from my iPhone after I get done listening to it.

I have about 30 gigs of mp3's loaded on to my iPhone 3GS. I have some smart playlists (like all songs by a particular artist) and I have synced these playlists on to my iPhone.
This is a subset of my music, and I intend to load the others after I get done listening to these.
I could listen to these through the playlists in order, or shuffle them. In any case, I would like the iPhone's iPod and/or iTunes to remove the song from my iPhone as I get done listening to it. This way, the # of songs on my iPod will gradually dwindle and eventually I'll upload another set on to it. I will also avoid listening to one song many times.
How do I do this?
Can I keep track of which songs have been played and delete them off my iPhone manually? It will be a pain to have to do this manually..

I have some smart playlists that I use to fill my ipod with new music.
Such as,
Last Played is not in the past 15 days
Limit to 600MB selected by most recently added
Live Updating is checked in all of these playlists.
There are a lot of options in smart playlist criteria to help you do what you want.

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