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You can mimic what you want by using playlists instead if albums. A single track can be in lots of different playlists.
Still doesn't sound like a great way to save tons of space. Do you really have more than 5-10% of such duplicated tracks on your library?
B
You'd be surprised how quickly a larger library can run into this problem. For instance, I have George Strait's entire catalog. This means that I have, just offhand, "Baby Blue" on his album
Beyond the Blue Neon (where the single originated), the
Ten Strait Hits collection, his boxed set
Strait Out of the Box, his entry in the
20th Century Masters: The Millennium Collection series, and on his career-spanning
50 Number Ones collection. That's five copies of the same song. Even if I leave out the
20th Century Masters and
Ten Strait Hits (because neither includes any new material), there were only 11 out of 72 tracks exclusive to the boxed set and only one exclusive to
50 Number Ones.
Let's say I created playlists instead of syncing whole albums. Then the problem I run into is the variances in mastering. Who wants to hear a 1990s master of a song right before or after a 2008 re-master? Only the singles from the earlier albums have been re-mastered over the years, meaning I'd either have to stick with the earliest version for consistency's sake with the original album, in which case the more recent hits compilations would fluctuate, or vice versa.
And don't even get me started on being a Johnny Cash fan...!