I have the same issue.  Here is my solution:

I have a single iTunes library with lossless and lower bitrate tracks
in it.  All of the lossless tracks are checked; the lower bitrate tracks
are unchecked (unless I don't have lossless versions).  In Squeezecentre
settings, iTunes tab, I select the option to ignore checked songs.  That
way Squeezecentre just picks up the highest quality version of each
track.

Then to make sure the smallest version of each track goes onto my iPod,
I create smart playlists that only pick up songs with a bitrate below a
certain threshold (if your lossy tracks are at 256, just put something
less than 400), and sync those with my iPod.

It works pretty well.  Also, since I'm on OS X, if I get a new CD, I
have an Automator action that automates the import - imports lossless,
creates a lower bitrate version and unchecks the latter.

The only issue is that you don't get play counts synchronised properly
- but that's a pain with iTunes / Squeezecentre integration anyway.

Hope this helps.

M


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markcaines
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