There could be many factors at play here, but I wouldn’t be surprised to learn that money combined with copyright law peculiarities was the root cause of much of it. If you can rerelease an album, you can get more money. Many artists also have problems with their recording labels and producers. Taylor Swift has re-released several albums do to quirks in the copyright (to simplify, the old versions of the songs were owned by her record label, but the new versions are only owned by her, so re-recording and releasing them gives her more creative control and freedom from her old label).
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