iTunes Library Migration

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Greetings to all here on Mac Forums!

My name is Doug, but you can also address me by my handle (and favorite season - which I can't wait to arrive - just got a huge dump of snow here in northwest PA :( ).

I'm going to come clean and get these confessions out of the way right now: I'm a MAJOR procrastinator and I'm an idiot when it comes to computers. Truth is, I should have joined this forum eons ago for assistance but I've let things slide for a long time. Here's a brief synopsis of my situation: I was a PC user up until 2011 at which time I bought my first Apple computer (an iMac model 12.2). I've had a lot of trouble with this machine's power supply, but that's a story for another time.

In 2016, I purchased my second iMac but actually didn't remove it from the box until this year (remember, I'm a procrastinator!). I'm finally in the process of setting it up and getting things moved over from my old Mac but I need some advice / assistance on how to go about it.

Specifically, at the moment I'm working on moving my iTunes library over to the new machine and I'm having some difficulty. Now I have an iPad, iPhone and the new iMac all on the 'iCloud' (still not sure exactly what that is) so these devices seem to be linked together by it, but to varying degrees. Right now, I'm just concentrating on moving my iTunes library (of about 3000 songs and several movies) over to the new desktop computer. The thing is, when I use my Apple ID to log in on the new computer, all of the music that I have purchased shows up in the library of the new computer, but it looks like each song has to be downloaded from the cloud maybe? None of these songs have my personal data with them (like rating / play count) and none of the music that I've loaded into my library from CDs over the years is there at all. I would like to switch all of this content onto the new computer at once, so I almost feel like I need to get the purchased music out of the new iTunes library (so it's not there twice)...

It would seem a logical step might be to set up iCloud on the old computer, but this may not be an option... I've been searching for iCloud (like in applications and then in the App store) and I'm not able to find it. The closest thing I can find on the old computer is something called 'Time Machine' - would that help?

OS stands for 'operating system,' correct? So do the operating system versions need to be the same to make this switch? The old computer is OS X (version 10.6.8) and the new computer is OS X El Capitan (version 10.11.6). Neither of these are the names of animals or geographic locations... is this an issue? Maybe I need to download new OS's? Like 'Mojave?'

Sorry for my ignorance... hopefully someone can help me out here. I can provide any info that you need, just don't know what that might be and I don't want this post to grow too long. Thanks in advance!
 
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Your Mac's Specs
M1 Mac Studio, 11" iPad Pro 3rd Gen, iPhone 13 Pro Max, Watch Series 7, AirPods Pro
When you set up the new iMac, you should have migrated your information from your old Mac.

https://support.apple.com/en-us/HT204350

If this is what you want, then you can boot into Recovery, and erase the drive, then reinstall the macOS version that came with that iMac from the Recovery partition as well.

https://support.apple.com/en-us/HT201314

In my opinion, this would be the best way to get all your "settings/ratings & personal" preferences for all your data.
 
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When you set up the new iMac, you should have migrated your information from your old Mac.

https://support.apple.com/en-us/HT204350

If this is what you want, then you can boot into Recovery, and erase the drive, then reinstall the macOS version that came with that iMac from the Recovery partition as well.

https://support.apple.com/en-us/HT201314

In my opinion, this would be the best way to get all your "settings/ratings & personal" preferences for all your data.

Thanks for the suggestion and helpful links ferrarr. If I want to couple my macs together with a hard link for this operation, what would the cord be called and what would it look like? Thanks, Doug
 

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