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After upgrading my drive I immediately uploaded 18gb of files on one go.
All files were in \artist\album\music structure.
I did not have any trouble with the transfer other than how long it took.
Selecting Random does seem limited to one USB drive transfer.
I've gone back to using a USB 128gb flash drive in the center console instead of uploading music to the SSD.
The upgrade was still worth it though.
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