While I love my iPod, I hate the iTunes software that “must be” used to synchronize my playlists.

MediaMonkey to the rescue. With hundreds of iPod refugees abandoning iTunes, the MediaMonkey community has several synch guides to help people make the transition. I wasn’t concerned about retaining play counts and ratings, so it was even more simple for me.

I had a unique need that I didn’t think could be automated. There are a couple of local radio shows I like to hear, and the national podcast versions cost money and don’t have the local weather, commentary and yes, even local advertisements that I want to hear. I found that I could record the live streaming shows to disk using RadioTime’s Red Button software. But copying them to my iPod was a manual affair.

But MediaMonkey has a paid version with a feature I love: advanced autoplaylists. MediaMonkey’s advanced autoplaylist feature allowed me to specify the folder I save the radio shows in, and synchs the shows automatically to my iPod. It does a lot more, of course, but this feature was especially nice for my needs.

My music is now stored on my Windows Home Server and synchs well to my iPod using MediaMonkey. And the interface for MediaMonkey makes sense: you can highlight songs and press ENTER to get them playing in an ad-hoc playlist.

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