In honor of the Day Against DRM, a long rant:

For my old job, I drove a half hour each way and listened to music and podcasts on my Archos jukebox. It was an MP3 player that also did video long before Apple came out with the iPod. Unfortunately, it wasn’t very easy to get video in the right format, so I rarely took the time to mess with video files. It doesn’t matter anyway now, because it recently died.

With the new job, I take the train and a bus for an hour-long commute each way, so my digital world of entertainment has really opened up since I can now add video to the list. I figured I’d finally take the plunge and take the iPod test to see if it’s really as great as everyone says it is. I bought one of the new iPods, purchased a couple of TV shows from the iTunes store, ripped a DVD of a movie I’d recorded off my cable movies subscription, and downloaded a couple of video podcasts. My hope was to combine music, podcasts, audiobooks (obviously from my personal library, not my local public one since I can’t check out audio ebooks for my iPod from my public library), and video in one device. A thousand digital flowers would bloom for me on my commute, and the most difficult part was going to be deciding what to consume each day (in addition to reading books and magazines).

You know, of course, that reality does not resemble this. The music works, although the fact that I can’t just drag and drop folders of music I’ve created during the last eight years (especially as playlists) is incredibly frustrating. If you don’t start out as an iTunes user, the iTunes experience is not a very satisfying one. Don’t even get me started on how I have to scroll through every single artist….

No, the problem is the video. I’m trying to be legal and buy video through iTunes (although I did also grab a couple of TV episodes they are offering for free), but the legal video won’t play. My ripped DVD is fine, as are the video podcasts. It’s only the stuff I’ve paid for that displays a black screen and no video.

Long time readers will remember that it’s around this time of year that I usually find myself in DRM hell for one reason or another (2002 was a particularly bad year), but this one really takes the cake. The hardware is fine, and I have no other way to get legally purchased video onto the iPod because of Apple’s Digital Rights Management (DRM) software.

In fact, I think the DRM software is exactly the problem. My iTunes software was originally associated with someone else’s iPod, so my theory is that for whatever reason, iTunes won’t recognize my new iPod as being mine, associate it with the content I’ve purchased, and transfer it properly so it will actually play. I’ve checked the knowledebase but it’s been no help. I’ve tried deauthorizing my laptop, restoring the iPod to its defaults, and reauthorizing my laptop, but nothing works. I’ve been to the Apple store twice, only to be told that they can’t do anything and I need to call AppleCare. Which I get to do once. After that, they will charge me for support to fix the various video files I bought from them that won’t work on their device that I bought. Yes, I’m limited to one phone call, like a prisoner in a jail cell. Alternatively, I could pay $59 a year to call multiple times to resolve this and any other problems that come up.

There’s also no way to create a new account, associate the iPod with it, and transfer my purchased content to it. Apple just doesn’t have a provision for this. I guess everything is just supposed to work the first time.

I can’t blame all of my DRM hell on Apple, though, because I’m also spending time in a special circle of Windows DRM hell. Dante had nothing on modern entertainment. I’ve also had to shift my media habits at work. I now have proof that I am less productive when I don’t have a TV or music on in the background. I’ve become one of those “partial attention” people who needs a background distraction in order to concentrate on a foreground task. I was lucky enough to get a laptop at work (since the departments I work for are on different floors), but the docking station for it does not have an audio jack. I didn’t know such a thing was possible, but it turns out I was wrong about that, too. It’s like there is no soundtrack to my life, and I find it very distracting. So when I’m sitting at my desk, I have the choice of being ergonomically correct (using a monitor, keyboard, and mouse) or listening to music. Goodbye Pandora, which I was really starting to enjoy. (Of course, it’s not just music. I can only watch but not hear content such as this 24–minute video about the future of publishing, which is actually applicable to my job… I think – I can’t be sure until I can hear it.)

So in order to be more productive at work, I decided to try Rhapsody’s “portable” subscription service Rhapsody-to-Go, which means I can transfer music at will to a Windows-based device and take it with me as long as I stay subscribed to the service. Of course, it doesn’t work on an iPod because the DRM is based on Windows Media Player, and the 2GB SD card in my Treo just isn’t big enough for my voracious music appetite. So I bought a refurbished, 5GB iRiver H10 just for this purpose. Yes, it’s crazy that I should have to do this, but there is a lot of music I would like to listen to but not necessarily purchase/own, especially at Apple’s or Rhapsody’s prices. (I do buy some stuff from All of MP3 and eMusic, but the selection just isn’t wide enough at either service.) I figured I could now also download audio ebooks from my public library since it subscribes to ListenIllinois and offers netLibrary and OverDrive titles (which are Windows DRM-based files).

So in order to partake of the digital entertainment feast and feed my media habits, I now have two players, plus my Treo. It’s divergence, not convergence. But, I’ll always have something new to listen to, so that’s a big draw for me.

So I waited not-so-patiently for my iRiver to arrive, ripped it open when it appeared on the doorstep, upgraded my Rhapsody subscription, installed the iRiver, started picking out music, and transferred it all over to the device.

Except, of course, it didn’t transfer. It took me four hours with three different techs on two phone calls and an email exchange to finally fix the Windows DRM on my laptop enough to transfer the music over. At first, Rhapsody kept telling me that it needed to upgrade a Windows DRM component, which it would then say it successfully did, except the error message kept popping up when I tried to transfer music and I got caught in a loop.

Eventually, though, Rhapsody’s tech support did solve the problems with instructions for upgrading various pieces of software on my laptop and on the iRiver (even though I thought I had already done some of these things), and I was able to load a couple dozen albums for my listening pleasure at work. I was a halfway happy camper, waiting for the right time to call AppleCare and not waste my one phone call. I went to load some more albums on the iRiver a few days ago, though, and all of the transfers failed. I didn’t have the energy to deal with it until last night. I’m not sure why it suddenly stopped working, but I started getting an error message that said the license for the music had expired, and it wouldn’t play. With this service, you have to connect your player to the Rhapsody server once every 30 days in order to maintain the license for the music on your player or it expires. I haven’t even had the iRiver for 30 days, and yet someone how music files were expired, and it wouldn’t renew the license. The answer was to reinstall the firmware on the device but naturally this reformatted it, which means all of the music I had already loaded was erased, and I had to start from scratch to add it all again.

So Rhapsody-to-Go is finally working (I’m lighting candles it will stay that way), but my quest to be legal (especially with video) is still completely stalled and I have the equivalent of a 3rd generation iPod because I can’t get the video to work properly on it. Sadly, all of this would probably go much faster and free up my time if I just downloaded unprotected music and video off the internet and transferred the files to my iPod or iRiver. It shouldn’t be this difficult, and I have to wonder how often the average user just gives up when faced with these DRM nightmares.

When I have further time, I’m going to write up my adventure moving to HDTV (to complement Karen Schneider’s). It’s tough being a media consumer these days.