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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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I’m always amazed by the Apple Fan Boys, because any time I’m forced to deal with anything from Apple I end up wanting to tear my hair out. Great hardware, but their software is written by the devil.

In preparation for the new system that is coming, I’m trying to head off the pending disaster that is moving iTunes to a new computer. Horror stories abound about this process, and nearly every tutorial out there has been written by someone who has obviously not done it. But I wanted to start organizing now, and try to head off disaster.

I copied every music file to my MediaSmart Server’s “Music” network share. It is organized by Artist / Album in folders. After spending time doing that, I think a fresh install of iTunes will work fine.

But I read a tutorial, from an Apple fan of course, who said to just consolidate your library and then copy that folder over when the new system comes. Well, that sounds easy. But, as with all things Apple, not so much.

Consolidating your library in iTunes means that the program copies all your music files registered in the program from their original locations and puts them in the /My Music/Itunes/Itunes Music/ folder. That sounds nice! So clicking on “File * Library * Organize Library * Consolidate Files” started the process. Then it stopped. With the error message “Copying files failed. The filename was too long or invalid.” But without any indication which file it was, so you are completely in the dark.

Because you can’t rely on Apple to actually fix a problem, you search the various fan sites for a solution. You find this problem has been around since iTunes was introduced, so it must be a “feature” in Apple parlance. And the solutions are either extremely time consuming or ineffective. You could go through your library and select a few songs at a time, right click and select “Consolidate Tracks”. At least that way you know its in that selected group. So I tried that … but it only finds the first one as you narrow down to smaller and smaller groups of files. And iTunes’ non-standard way it treats highlighting and the arrow keys will drive you crazy. One enterprising programmer wrote a little javascript program to tell you that it can’t find the filenames that iTunes is choking on (a valiant effort, but to no good effect).

You can also wade through the XML file to try and find a path that isn’t to the iTunes folder, but that takes forever; every song has about a dozen lines of code in that XML file.

So for me, the solution will be to point a fresh installation of iTunes to my network share and “consolidate” from there, so it copies the files to the local drive. That is, if that will even work.