Quite frankly, Monty, I find that none of that is a problem using Windows XP, (although this old system can't read cards over around 30gig or less), never mind a newer OS. The only time I had similar issues was way back when I first got my 380 and used the 'internal' file operations on the player. This simply didn't work and would corrupt files, lose music and at times make an SD Card unreadable (by the player). So I reverted to hooking the player up to the PC and using my file software. I have never had a problem using a windows computer. However, I find it hard to believe that AK iRiver would make a product that can't be easily managed by the millions of apple users in the world. My sympathy for the problems you are experiencing (and I feel guilty, now, for extolling the virtues of the ripper to you before you got it).