Can I measure size of checked tracks only?

I have a library bigger than my iPod Classic 120 can fit, so I rotate tracks in and out by using the "synchronize checked items only." To add tunes to iPod, I have to un-check a similar amount of files within the library. Since I trade off a dozen or more albums at a time, sizes vary (length and bitrate, mp3 or lossless, etc.) Plus, the library itself is still growing.
When synchronizing, iTunes will give the familiar "Not enough room, will add as many tracks as possible" message, but I never know how much I need to un-check (thus deleting from iPod) to fit. Also cannot identify which items are not added due to space.
Will sometimes get a message like "Cannot synchronize, need 2 Gb of space, only 1 Gb available." This measure does not account for songs to be deleted.
Is there a way to measure the size of all checked items in iTunes before I synchronize?
Thank you for any suggestions!
Barry

You're welcome. You could also consider not using unchecking at all. Another method you can use to auto-sync your iPod with iTunes is "Sync Music - Selected Playlists". Syncing selected playlists is just like syncing your whole library only on a smaller scale and more "selectively". This is particularly useful when your library is larger than the capacity of your iPod. When your iPod is is set to sync selected playlists it automatically picks up any changes you made to that playlist in iTunes since you last connected. Anything you added to the playlist will be added to the iPod, anything you deleted from it will be deleted from the iPod. In other words the iTunes playlist and the iPod are kept "in sync".
Open iTunes and create a playlist to update your iPod from, call it -My iPod for example (the dash will position it at the top of the playlists in Sources). Drag whatever content you want to have into the playlist. Now connect your iPod and when it appears in the Source list click on the iPod icon to bring up the preference tabs in the main pane. Go to the Music tab and choose Sync Music and the Selected playlists radio button. Choose the playlist you just made from the selection and click Apply. You can also sync from any existing playlists by choosing the same setting, you just need to make sure that the size of the playlists don't exceed the capacity of your iPod: Syncing Music to iPod
Using unchecking to manage an iPod is an option (and works fine when you are working with a small number of specialised tracks such as Christmas songs) but only if you can live with the other things unchecking does:
Unchecked songs will be skipped when playing songs from the library or a selection. They will only play when individually clicked on.
Smart Playlists have an option that unchecked songs won't appear.
Unchecked songs will not be burned to CD.
Genius and iTunesDJ will not use the songs that are unchecked.

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