#3 - you never know if your hard drives are going to fail and you lose all your digital music. At least with the actual cd you can always rerip.Just back up your music? Just drag and drop if not automated.
External USB drives are cheap. 1 TB USB 3.0 for $79 shipped, 3TB $130 ... What happens when your transport goes especially a CD Player is the more complicated and $$ issue IMO.