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I’ve never been so frustrated with a piece of software as I have been with iTunes lately.

NOTE: Yes, I work for Microsoft.  Yes I’m aware they make the Zune.  I’ve got years invested in hardware with iPods, and until someone makes an OEM integration kit as good as what I have, I can’t switch.  Truth be told, from a portable device player, I *do* think the Zune is better.  But let’s just leave that out of this argument for now.

In my home there are roughly 4 iPods floating around.  We have a library of over 5,000 songs both popular and not that are in our digital library.  That digital library is mostly MP3s, mixed with some iTunes purchased songs (although not since Amazon MP3 began).  That library sits on a shared drive on my Windows Home Server so it can be accessed through various streaming means (Home Server streams to iTunes software, XBOX, etc.).

Also in my home are roughly 6 computers ranging from desktop to laptops (mostly laptops).  These are used between my wife and myself (and one for the kids).

We all listen to music on our devices and via our machines.  We all want to listen to the same library, create our custom playlists and have them available everywhere.  We all want to be able to sync on whatever computer we want, but we’ll settle to be tied to one that you can pair with.

iTunes…sucks.

Yes, I’m looking at you iTunes.  I’m aware of the other options like Songbird, etc. but frankly I haven’t tried them out yet.  If you have and they will solve my woes, can you share your experiences?

Why does iTunes suck?  Easy…

  • It assumes 1 user/1 computer – the “library” is a local and static library unless the user interacts with it.  What I mean by this is it does not have the ability to monitor folders (like pretty much every other software out there for media does).  I want to point my iTunes library to my server share and whenever I add music to it via other computers, that other ‘libraries’ will be aware of it and just add it to my local library.
  • Portability sucks – try to transfer your iTunes library to another computer.  I dare you.  Navigate through all the Apple support suggestions and hacks online.  Frankly unless you are Mac to Mac migrating, it is not easy for a healthy configured library.
  • Not informative – one of my biggest issues is that when I configure the library to be a mapped drive (let’s say M:), if M: is not available for some reason, iTunes decides on it’s own without telling me that it is going to switch the library back to the local volume/hard drive.  Any future action (i.e., iTunes purchasing, Amazon purchasing, etc.) now doesn’t save to my server library.  WTF?!  Can you at least tell me: Hey user, that location you set for your library, ‘M:’ is not available right now…what would you like us to do.  Stop moving it around for me.
  • Home Sharing – what is this supposed to be again?  I thought this would save me.  I could have at least one place that would be the library and home share to other clients who could then use this feature to sync.  Um, nope.  This is basically the sharing they already had except with a new name.  Worthless.

I wish the iTunes team would put in their lab 3 iPods and 4 computers with 2 users and a library stored on the server.  Work toward making your software work in that environment as seamless as it does with 1 user and I’ll be happy.  Until then I have to navigate your changes and try my best to explain to my wife why the music we bough on the desktop is not on her laptop until she adds it to the library that is already mapped to the network share where the music already exists.  Yeah, that’s what I though.


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