Is it possible for me to keep my iTunes libraries in sync with each other on OS X and Windows if so how? My iTunes library is stored on a network share made available via AFP and SMB. Is it possible for me to make it so that any changes made on iTunes on Windows are also shown in OS X and vice-versa or will I have to maintain separate iTunes Libraries resulting in a clunky mess (especially when iTunes Match starts uploading playlists twice and other things)?
MacOS – Keep iTunes library in sync on OS X and Boot Camp (Windows 8)
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Home sharing should allow you to see each other's libraries over your home network, and drag apps from your wife's onto yours and vice versa. You can definitely do this despite having two accounts - my wife and I have a similar problem. You may have to enter both passwords from time to time to authorize purchases, though.
I found some help setting this up from "Activating Home Sharing in iTunes".
I believe you can also sort hers by "items I don't have" so you can see what she might have bought of interest to you, although I'm not sure you can automatically sync them.
This SuperUser question seems to suggest that merging two accounts is not an option:
Can I merge 2 iTunes Store accounts?
iTunes preferences are stored in
~/Library/Preferences/com.apple.iTunes.plist
I presume you access your two libraries by launching iTunes while holding down the Opt key.
An alternate method to launch iTunes and swap out pref files at the same time would be to make an Automator or AppleScript app that switches pref files, and makes a link from ~/Music/iTunes to one of the libraries, then launches iTunes for you.
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Best Answer
Later edit
See iTunes: Moving iTunes Files (Self Managed) for a better explanation of how to achieve dual, almost-in-sync libraries across different machines
[This is not a hugely technical explanation, more one of the frustration I've had doing the same thing... if you want more details, ask...]
You can share the file location, but both machines will 'see' it differently. iTunes uses absolute references [truly irritatingly] so the only way to keep the Library in sync is to either add the same files to both [not good if it's supposed to be self-organising] or to manually copy the iTunes Library.xml file & use BBEdit to change the path structure for every entry - which can be done but then may take the Windows version of iTunes up to 10 hours to process it.