Iffy
I am yet to try this, But I have seen it done. It's a pain in the but and requires a computer, so it really would not be worth it, but I'll put it out there anyways.
Basically, pictures dont not have the 3 day/3 play limit, so on a computer change the song name from, lets say DM.mp3, to DM.jpg. Send the song, and the other person can then change it back and play it as they wish.
This is a hasstle, however It can be done. Possibly with the release of Zune Linux (sorry to change the subject but I am quite excited about its release whenever it may be), this can all be done from the Zune.
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