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In relation to the application… Still no resume playback for iTunes (renamed as Music now), which was available on SoundJam MP 2.5.3, from which iTunes was developed in 2001. Almost 30 years later, it is not yet available in the latest iTunes/Music.

What I meant is that you are listening a very long playlist of thousands of songs, quit iTunes, reboot the Mac or shut down the Mac. The next time that you open iTunes it starts from song number one again, but you want it to resume from the last song played (say, song number 1456 or whatever). For me that is the most essential feature missing in iTunes/Music.
 
I feel like I’m the only one I know who buys music. Everyone I know streams either free or YouTube or pay for Spotify or Apple Music.
 
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It uploads all your personal MP3s to the cloud allowing you to stream them in the music app. Apple Music includes this but you can still pay the $30 a year for Match instead to include your ripped CDs with your store-bought music.
I don't see the point in Match any more. I re-ripped all my CDs to Apple Lossless during the pandemic. No need for lower quality matches of them. And I re-torrented all the stuff I wasn't gonna buy in lossless too.
 
I don't see the point in Match any more. I re-ripped all my CDs to Apple Lossless during the pandemic. No need for lower quality matches of them. And I re-torrented all the stuff I wasn't gonna buy in lossless too.
I can see how it's not a fit for a lot of people, but I love having it and have subscribed since day one. I'm glad they didn't remove it over the years. It's convenient to have all of my music available on all of my devices whenever I need it, but to also not have to pay $10 or more per month for a streaming service.
 
I can see how it's not a fit for a lot of people, but I love having it and have subscribed since day one. I'm glad they didn't remove it over the years. It's convenient to have all of my music available on all of my devices whenever I need it, but to also not have to pay $10 or more per month for a streaming service.
I use this neat trick called "copying it over the network".

It's free.
 
I use this neat trick called "copying it over the network".

It's free.
Like I said, it's not for everyone. It always surprised me when people think their way is the only way to do something. As if people weren't aware of the fact that you could just copy stuff over the network.

It's awesome that works for you. But I'm not always at home when I want to listen to something. If I'm out on a bike ride with just my watch and I want to download something, it's worth $30/ year to me to have that option. Just doing everything at home, when you are on your network, doesn't always work for everyone's use case.
 
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I didn’t purchase music from Apple until they increased the bitrate in the later years. I didn’t want to pay for music that was only 128kbps.
If you purchased 128kbps, I think you should re download them. They should be in better quality. Apple did increase bit-rates at some point.
 
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Still utilizing iTunes as my library everyday and no major complaints. Offers a lot of flexibility in organizing my collection as I want it to be. Some good features. Now and then also purchasing some new music but that is a clumsy exercise due to neglect by Apple.
 
You forgot, or maybe didn't have time, to mention two important things in iTunes history:
- abandoning DRM (a huge battle by Jobs and, nowadays, alas, no longer a thing with streaming)
- the increase of bitrate which Apple did at a certain point (don't remember the year) where you could pay a difference and own higher quality music. I specifically remember that because it cost me an arm and a leg...
the mastered for iTunes initiative was also important, if underappreciated.
 
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