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).
Streaming apps (like Spotify) do things to songs that are uploaded that end up making changes on how the songs sound like (compression & signal processing).
The remastering wave is largely due to adapting to these standards as streaming became the default way to listen to music. Many of the old recordings were not meant to be listened through spotify and didn’t sound like the way they were intended to be heard, hence the remastering.
2005 was the peak in the loudness war. Regardless of the quality of a song it always sounds better the louder it is. So when you listen to songs on the radio or in the record store it sounds great at high volume. But when you have bought an album and get back home and listen to it after adjusting your volume it does not sound as great. And if you listen to two songs one after the other with the same settings the louder of the two sounds better.
So in the early 90s when digital recording became standard and CD were making its way into the market audio engineers started playing around with how to make their songs louder. There are physical limits to how loud you can make a recording. But if you reduce the dynamic range making the quiet parts as loud as the loud parts you can make the song louder on average. And this peaked in 2005 but songs were pretty loud with low dynamic range all the way from the 90s until the mid 2010s. With bands such as Nirvana and Daft Punk on either end of the loudness wars demonstrating how good songs with lots of dynamic range sounds. It also helped that streaming services started setting the volume based on the average volume of a song rather then the loudest part, which also improved dynamic range.
During the loudness wars a lot of earlier songs were remastered to comply with the new loud standard. And then after the loudness war all the songs that had been mastered in this way had to be remastered to introduce more dynamic range again.
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