How to use old iTunes library from external hard drive on new MacBook Air

I'll start with screen shots if iTunes on my Old Mac. Somewhat by chance, after returning home and turning on my Old Mac, I forgot to turn on the G-Drive before accessing iTunes. With the external hard drive off, I tried to access Around & Around by the Grateful Dead. When I right clicked to access Song Info to take a look at the audio file's location, I got a message that the song could not be found (1st screen shot), which made me remember to turn on the G-Drive. However, before doing that I thought to see what the Song Info said about the location of the audio file with the G-Drive turned off. Turns out the location is file:///Music/Grateful Dead/...(2nd screen shot). When I turn on the G-Drive, the location of the file shown on song info changes to /Volumes/ITUNES G DRIVE/Music/Grateful Dead/...(3rd screen shot). I also checked iTunes>Preferences>Advanced>iTunes Media Folder Location under both conditions (i.e., G-Drive off and on). As you can see in 4th and 5th screen shots, they are identical with no location shown for this folder under either condition. I've got additional screen shots if needed of Finder on my Old Mac showing the location of iTunes and similar screen shots for how things look on the New MacBook (things look different as expected.)

I find all this very interesting and know that when I set this system up on my Old Mac approximately five years ago, I did some serious research on how to get iTunes to perform this way with the G-Drive, and it's performed flawlessly ever since. It's just doing all this great stuff on old machines and I'm stumped on how I set this up or how to transfer the setup over to my New Mac.

Thank you for this helpful information, tt2. In fact, it was my reading of your Make a split library portable - Apple Community that prompted these questions. I'll review this information in depth once more to take steps to get my iTunes library in the right shape for portability. I do have two somewhat basic questions as I begin this process: 1) on my old iMac, how does iTunes currently know to look at my old G-Drive to find audio files since in Preferences>Advanced there is no location being shown for iTunes Media Folder Location, and 2) where do I rearrange and repair my iTunes library, on my iMac's internal hard drive or the G-Drive? Reason I ask is that I don't know how to list all my audio files in an iTunes Media Folder on my iMac since it is a 500gig machine and I have 835 gigs in audio files. Any info would be greatly appreciated!

Ah, the proverbial mystery! I’ll forward screen shots early next week after returning from a short trip.

Thank you for the additional info and it’s a relief that my intuition was correct that the library fix happens on the external drive.

This is very helpful-I'll take these steps this evening and let you know the results. To answer your question, the iTunes Library.it file is located here on the Old Mac

The iTunes Library.it file is located at the same location on the New MacBook Air

Unfortunately, I don't believe I can use my old G-Drive with my new MacBook Air as the library folder for iTunes. This is an older model G-Drive that I've had for about 6 years. It only comes with a Firewire 800 and mini-USB connectors for transferring data. I tried using a Firewire 800-to-USB cable to connect the old G-Drive with my New MacBook Air, but consistently got a message saying there was insufficient power (mind you the old G-Drive is plugged into the wall.) After explaining all this in some detail, the good folks at the Apple store did not think the old G-Drive could successfully be connected to their new MacBooks. That's why I got the new G-Drive and started moving files over from the old G-Drive (ITUNES G DRIVE) on my Old Mac to use on the new MacBook Air when the problem started. It would be great if there was someway to address the connectivity issue for the old G-Drive; this potentially might solve all these problems.

So, it sounds like what I should do, in lieu of getting the old G-Drive to connect to my new computer, is make a copy of my active library files and the other steps you mention on my new G-Drive. Only question I have before starting all this is where do I find "option-start-iTunes" to get iTunes to connect to that copy of the database?

OK, using my new external hard drive (G-DRIVE 2019) I've followed instructions all the way through the media folder becoming /Volumes/G-DRIVE 2019/iTunes/iTunes Media. I've also confirmed that I'm using the most current active set of library files and that my content still plays. After clicking OK for the new media folder location, iTunes is asking about consolidating the library. I just want to confirm what comes next before clicking YES. Here's the current screen shot

So, if I click "YES," this will begin the process of moving all of the audio files off the old G-Drive onto the new G-DRIVE 2019? Will the audio files be removed from the old G-Drive, rather than copied over? Reason I ask is that I want to maintain the Old Mac using the old G-Drive as a music server when needed for as long as possible. If the audio files are moved rather than copied, I imagine I could manually copy the files back over to the old G-Drive from the new G-DRIVE 2019, disconnect the new G-DRIVE 2019 from my Old Mac and then reverse the process to reselect the original library and reset the media folder location to blank (or maybe /Volumes/ITUNES G-DRIVE/Music/. Please let me know if I'm on the right track here and I'll be off and running...

Success on all fronts!

I'm now the proud owner of a self-contained portable iTunes library-all due to your detailed instructions patiently delivered. I've chosen a new iTunes library off the new G-DRIVE 2019 for the New MacBook and the media location automatically filled in on Preferences>Advanced. For the first time, I played lots of tunes from all over my library on my New MacBook. On the Old Mac, I reversed your instructions, choosing the old library off the old Mac's internal hard drive. Preferences>Advanced automatically reset the media file location to blank-I suppose to allow the "mystery operation" to take place-and then iTunes played content off /Volumes/G-Drive, the old external hard drive!

Thanks again for sharing your expertise and time to help solve this puzzle.

Everything has been working fine with iTunes on both computers. The next step for me is keeping my library up to date with new music. I normally buy CDs and upload them to iTunes. Today I tried to upload a new CD to iTunes on my old 2011 iMac and I suddenly got this message

Following these directions, I accessed File>Get Info for the Music folder, iTunes folder, and iTunes Media Folder on the iMac's internal hard drive. Here is what permissions look like for these folders in Get Info

So, with all the permissions showing both Read & Write, I don't know why this is occurring. Of course, all this occurred AFTER I successfully created the new self-contained portable iTunes library for my new MacBook Air. I now want to begin updating my library in two places by uploading new CDs to my library on the old iMac and then going through the transfer process you described to bring the audio tracks and newly configured iTunes library over to the new MacBook. I don't plan to do this very often (I buy about 30-50 CDs a year) but thought I should try the process out before too much time went by. I'm taking these steps because my new MacBook doesn't have a CD reader and I don't own one to attach to the MacBook. Perhaps an easy fix would be for me to just buy a CD reader and manage my library entirely from the new MacBook. Suggestions?

Thanks for the link, but quite honestly, I was only trying this as a way to see if permissions were correct on iTunes folders on the new external hard drive, and by extension, iTunes on my new MacBook. It was never meant as a work around, and given how involved this remedy appears, it's not how I want to end up with iTunes. The external hard drive is meant for the new MacBook, not for the old iMac. The real work around if all else fails on my old iMac is to buy a CD reader for my new MacBook and move the whole iTunes operation over to that computer from the old iMac. It's not what I was hoping for but it might be my only choice if I want iTunes to function properly.

This is a response to your second post.

Before responding back to you yesterday I re-checked all settings on Get Info for the iTunes folders AND reset all permission to Read&Write for all users and used Apply to enclosed items for these changes on the old iMac. Still nothing-I can't upload a CD into iTunes on the old iMac-very frustrating after all we went through to create the new library. Interestingly, on the old iMac I can still edit song info for individual tracks in iTunes, can create playlists, can change import settings, can move songs around; I even deleted a track from the library-no problem. Uploading a CD, forget about it!

Any final ideas on how to fix this? I'm fast approaching retiring the old iMac because of these issues. I've also been kicking around purchasing a more serious music server with the hope of avoiding all this in the future the next time I change machines.