Free to try (can only copy one file each time, doesn't suppport batch copy); $29.95 to buy (Buy it now)
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Macsome iPod Transfer can transfer files among ipod, iPhone, iTunes and Mac. It is a iPod file transfer tool which can transfer iPod videos, copy music and more from Mac to iPod. Meanwhile, it also can transfer iPod music, videos and photos from iPod to Mac, backup iPod to Mac fast and smoothly. Easily copy files from ipod to ipod. High ripping speed and concise interface design make iPod/iPhone content management simple and convenient on your Mac. With it, you can transfer Audio, Video and photo from iPod to Mac, transfer files between iPod and iTunes, copy files from Mac to iPod without iTunes, manage playlist on your iPod and so on. It can protect your iPod against unwanted iTunes synchronizations. It also supports showing all informations about your iPod/iPhone.
What's new in this version:
Fix a bug that may fail to copy multiple files from iPod to Mac.
I see no "pros" at all for this product. This is a terrible product. See below.
Documentation is grossly deficient; won't work on Touch 4th Generation but doesn't say so; recognizes my Classic 160GB, but ERASED all content without the user knowing it; then corrupted the software so my MacBook Pro could NOT see it; had to be restored; none of this is documented; and to pour salt on an open wound, they haven't yet acknowledged or replied to my email support letter; and they don't show a phone number either. Do NOT try or use this product at this time.