iTunes is a fine program in many ways, but its designers seem never to have considered how it might be used in a family situation, or even by a single user with multiple computers. Just because you have multiple Macs, or use a Windows PC at work, doesn't mean you want each one to have a completely independent iTunes library. Unfortunately, moving music, movies, and playlists from one library to another is a hassle.
Enter SuperSync, from the company of the same name. Its claim to fame is that it can synchronize two or more iTunes libraries on networked computers - across a LAN or the Internet. It can move the music files themselves, update iTunes, and even update just metadata changes like play counts, ratings, and so on. The program is extremely flexible and customizable, which can make for a complex interface, but that's a small price to pay for being able, for instance, to synchronize just certain playlists, or only videos in .m4v format. And the fact that you can do it bidirectionally means that you don't have to worry about changes on one Mac being overwritten by changes on another. SuperSync even works under Windows, if you want to sync your Mac's music with your Windows machine at work. Other useful features include the capability to compare and merge libraries, find duplicate tracks and corrupt files, access your music library over the Web, and listen to your music from an iPhone, iPod touch, or even TiVo. SuperSync costs $29 for a 2-pak version, $39 for a 5-pak, and $49 for a 10-pak, but you can enter to win a 5-pak in our DealBITS drawing this week.