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Is there any delay in browsing/playing files on car startup with the library your size from the HD?
I remember a few years ago when trying to pull off the same thing with around 2k tracks on my Alpine headunit was a headache, it would take about 20 seconds just to dock (scan) the files on the drive and that was with just with a sample of my whole library lol.
I think when you have a library bigger than 1k songs and loads of playlists its just easier to use iTunes + iPod as everything is stored in its own library database which most cars can read.
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