Crossfade Playback & Unchecked Songs

The crossfade playback functionality works quite well and does what it is supposed to do except when the playlist contains both checked and unchecked songs. There's no crossfade at all when an unchecked song is encountered before moving on to the next checked song (I hope it's more or less clear what I mean).
Is there any way to get around this?
iMac G4 Flat Panel   Mac OS X (10.4.5)  

Rather than checking and unchecking tracks as your primary method of controlling what goes on the iPod, instead check your entire library then use playlists and smart playlists to group your stuff and you can then set up the iPod to ONLY sync playlists you pick.
For example, you might make a Smart Playlist limited to xx number of songs or xx gigs or whatever you want and the playlist is the stuff "Least Recently Played". Check live updating so this list is constantly updated. Now pick this as the playlist synced to your iPod. Each time you listen to stuff in iTunes or the iPod those items become the MOST recently played and will fall out of that list and be replaced with something new. Each time you sync your iPod, that list will refresh and you will get a constantly changing selection of stuff.
Of just create a normal (not Smart) playlist, pick that one to sync to your iPod and just manually add and delete stuff from it, keeping it under whatever space you have on the iPod. This gives you what you have now, but you can leave everything in your library checked.
Patrick

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