You cannot make iTunes synchronise the main folder across what is essentially two machines. Note: You are not going to be moving the default iTunes folder on either OS, only the Media folder location. I'm going to assume we're using the Mac as Master, Windows as Slave. One has to be "in charge" the other merely a copy. It is going to be very counter-productive if you keep adding tunes & playlists to both iTunes, as you will then never be able to synchronise them. The first thing to do is establish which will be your Master & which your Slave. It is not a quick task, but it can be done. You would have to do that manually, every so often. You can do it, but each copy of iTunes will want to be "in charge" & they will not auto-synchronise at all. "Sharing the library" is something of a misnomer when it comes to manually keeping one iTunes Media folder synchronised between two different machines & two different iTunes instances. Getting both Mac & Windows able to read & write to the same location is just the beginning…
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