Looking For iTunes Help

I thought I would use this forum to see if anybody can help me out. I’m looking for either an iPhone app, AppleScript, or a way to lay out a smart playlist in iTunes for a particular problem.

Here’s the background… I have a 16gb iPhone. I have an absolutely enormous iTunes library (almost 130gb… Over 28,000 songs). Obviously, I had to set up a playlist in iTunes just for my iPhone music. The problem that I’m having is that even with paring my library down to 9gb for the iPhone, between apps, pictures, podcasts, etc, I am constantly running out of room and having to delete music from my playlist in order to make it fit. And forget about trying to add anything new to the playlist. Purchasing a larger iPhone is out of the question right now for me.

What I’d like to do… I’d like to build a smart playlist (or get an AppleScript for iTunes) that would allow me take my iPhone playlist and mix it up every time I sync. Have it set to sync, say only 8gb of music, even though that particular playlist is 9, 10, or more gb. This way, I can keep adding music to the iPhone playlist and never have to remove any. Whenever I connect to iTunes, it would randomly sync only the set amount.

As an example, let’s say I have the following music in my iPhone playlist:

Song A
Song B
Song C
Song D
Song E
Song F
Song G

My iPhone can only hold songs A, B, C, D, & E

When I connect to iTunes, this program would randomly rotate out Song A and swap in song F. But the next time I sync, it might swap A back in while taking out B and adding G.

Hopefully this makes sense. Please feel free to leave a comment if you have any questions or ideas.

Thank you all for your help!

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