Delete unchecked songs

Since I have just over 40,000 songs in iTunes, I had an idea how to use Match and not exceed the 25,000 song limit.  When synching with my iPod classic, I have it only sync checked songs.  So, for me, it makes sense to put only those checked songs in the cloud, so I can access them from my iPhone & iPad.  That count is currently about 12,000.  What I want to do is create a copy of the library, delete all the unchecked songs (keeping the files), then turn on Match and let it do its thing.  I could then restart iTunes with the original library, where Match is turned off, and still have everything there.  As time goes on and I add more songs to the iPod by checking them, I can repeat the process.
I created a copy of the "iTunes Library.itl" file and named it "iTunes TEMP Library.itl". Started iTunes (11.0.4.4) with the new library and selected the smart playlist "Unchecked". The idea is to delete all the unchecked songs from the library, but of course, keeping the actual files. As a test, I clicked on the first song, then did a shift-click on a song 4 lines down, which selected 5 songs. I hit the delete button, but nothing happened. Tried right-clicking on this highligthed group, but don't have the delete option. Are we not allowed to delete songs when viewing them in a playlist?
I then clicked on the "Songs" button up top to list all songs, and clicked on the check-mark column header. This sorted the songs, with all the checked ones first. Scrolled down to the first unchecked song, clicked on it, then 4 rows down did the shift-click. Hit the delete button and was able to delete the songs, keeping the actual files. Shut down iTunes and started it back up using the original library. As expected, those deleted songs are still there.
So, now I'm looking for a quick way to delete all unchecked songs when I'm in that secondary library. Why didn't that work in the "Unchecked" playlist? Am I missing something obvious?

Thanks again.  Can't tell you how much I appreciate the tips and info.  Looks like everything is working as I expected.  Deleted all unchecked songs from the copy of the library, turned on Match and its well into the second step (Matching your music with songs in the iTunes store).
As far as those library files go, I've been thinking that it doesn't really make any difference to me.  I'll only use that copy of the ITL file for this matching process and to update to higher quality checked songs.  Then go back to the original library, with Match still turned off, for everyday use.  As I check more songs in the future, I can always repeat the process to get the latest ones in the cloud.
One interesting thing I just noticed.  My original iTunes Library Genius.itdb file is just 32kb.  I copied the iTunes Library.itl file to one named iTunes TEMP Library.itl, started iTunes with that library, and turned on Match.  Now the iTunes TEMP Library Genius.itdb is 29,468kb.  Based on the time stamp of the file, it would appear that this file grew during step 1 (Gathering information about your iTunes library).
Hope you have a great weekend!

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