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It's not a MAC or Windows issue, it's a "DRM" issue which goes back to the rights owner. Each Itunes download (well the ones you pay for) are protected with DRM; the music the movies all of it.
In 2011 a few really good DRM "rippers" came out but the industry quickly shut the software down and sued the authors who would not decease. So today you actually have to "capture" the output of Itunes content to make it multi-platform available.
With video you actually play it out of Itunes and record it on another app real time. with audio the best way is to "burn your playlist to cd" inside of Itunes then RIP the cd back into something common like media player.
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2021 Model Y
2005 Cayenne Turbo
2012 Panamera 4S
1980 911 SC
1999 996 Cab
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