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iTunes Match tips
My iTunes Match Track upgrading and process info:
If you have less than 25,000 tracks:
1. First let iTunes Match do its things and find all possible matches in your library and finish uploading any non-matching tracks.
2. Once its done, make a new Smart Playlist (I made a folder for all my Smart iTunes Match Related Playlists)
Name this one: iCloud-Upgradeable
Bit Rate is less than 256kbps
Media Kind is Music
Location is On This Computer
iCloud Status is MATCHED
iCloud Status is NOT Ineligible
Allow the Live updating to be checked.
Once this smart playlist is made, you will see all the tracks that have been matched and are less than 256kbps have been matched and have corresponding 256kbps versions in the cloud you can grab.
Now, you can do the next track or album or all at once, but select tracks from this list and hit Option-Delete:
The dialog that comes up asks you to confirm that "Are you sure you want to delete the selected item from your iTunes Library?" This item will also be deleted from any iPod, iPhone or iPad which synchronizes with your iTunes Library.
There is a checkbox for "Also delete this item from iCloud"
MAKE SURE that checkbox is not checked and go ahead and hit DELETE ITEM.
You will still have this in your library, but now it will play from iCloud, or you can highlight the track and right click and DOWNLOAD it and it will replace the old one you deleted, with a nice new 256kbps AAC encoded file from Apple.
To make the download process easier, make Two MORE Smart Playlists:
1. First one is named iCloud-Downloadable
2. Criteria:
MAtch ALL:
Location is iCloud
Location is NOT On This Computer
Media Kind is Music
iCloud Status is MATCHED
Now this will display all the files from the previous smart list that you deleted but left in the cloud.
Highlight them all and then right click and hit download and it will queue them all up to be downloaded to your local machine. Yay!
Before you start downloading make sure you have plenty of drive space, a little over 7000 tracks of 256kbps AAC files took up just under 80GB in my case.
I upgraded a few of my more obscure tracks/albums that showed as matches by hand and compared, and didn't find any mismatched files thus far. But iTunes only matched around 7500+ files out of 45,000+ tracks that I whittled down to around 14,000 files less than 256k.
The third smart playlist just helps you confirm you got them back:
1. Name is iCloud-Upgraded
2. Criteria:
iCloud Status is Matched
Location is On This Computer
Bit Rate is 256kbps
This should show you all the ones you upgraded and downloaded.
Couple extra tips:
1. I had way more than 25K tracks, so before any of this, I made a smart playlist that contained only music tracks less than 256Kbps, and then exported that playlist.
2. Quit iTunes, held down option and made a new library
3. Changed the location of the music library to another folder.
4. Turned off copy files into new location
5. Imported the exported playlist.
Now I had all my tracks that were less than 256kbps from my old library in my new one, but safe in that they could NOT be deleted (as they were in the old library location), but could be played, and also allowed me to use iTunes match just to match and upgrade all my music, as there is no way I was fitting my entire library in the cloud until they give us an option for more than 25k files.
I haven't worked out the exact process to re-integrate all the new upgraded 256kbps files back into my main library, but thats next. Will probably actually make playlists with just the upgraded files, and use BBEDIT to do a DIFF on the xml of the playlist and my main library, or applescript or something.
Also plan on going back in and deleting stuff from the cloud too once I hit the 25k song wall, and try re-encoding some of my lower than 96kbps tracks (that iTunes automatically excludes from matching) to higher than 96kbps and see if they match then, others have reported success doing that.
Here are some reference links I found useful:
There is also a tip in the comments on one of the above about changing some tracks from music to podcasts or voice memos if you have more than 25k tracks and don't want to split up or make new libraries - this prevents iTunes from recognizing them as music tracks, but still remain playable, get below 25k, and still retain all the metadata, etc.

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@AdeleB AdeleB commented Apr 28, 2014

Thanks for you tips. Also interested in iTunes alternative to transfer iTunes playlist to Android.

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