Convert playlist to lower bitrate without creating hundreds of duplicates?

So here's the issue:
I have an 8GB iPhone and nearly 14GB of music to put on it. 14GB is a lot, but most of the tracks are Apple Lossless, so there's only about 770 songs in the playlist. I know on the Shuffle, there's an option to compress a playlist to play on it, what about for the iPhone? I could easily just hit 256kbps AAC and select all the files in the playlist and convert them that way, but then I'd wind up with 770 lower quality duplicates in my Library. And a difficult way of identifying which is which to recreate the playlist. Does anyone have any solutions?
I've thought of a way. A smart playlist with the 770 most recently added songs, set convert, copy that playlist to a new one and sync that with my phone. That would work to get the music on my phone, but then what about the Library and the duplicates there?

If you are auto-syncing your phone with iTunes you have to keep the compressed tracks in the library. The only way to remove the duplicates from the library entirely is to manage your phone manually so that if you remove the compressed tracks they stay on the phone. You could also create a separate library for the phone to sync to and add the compressed tracks to it: Using multiple iTunes libraries -Mac
If you choose to remove the compressed tracks have a look at Doug's AppleScripts there are a couple of scripts there to help manage duplicates. Search the page for "Corral iTunes Dupes" and "Corral All dupes": Doug's AppleScripts for iTunes
Doug also has a shareware application called Dupin specifically for managing duplicates, you can get it here: Dupin
You could also delete the playlist that holds the duplicate files and the tracks along with it. Highlight the playlist, hold down the Option key and press the delete key.

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