I have a similar problem. Worse, actually. I'm on vacation and trying to access my music on my Pogoplug that's back home via my Android app. No music, using the music part of the app, shows up, but that's been the case for quite a while not. Not sure if that's my fault (mp3 tagging perhaps) or the device. But, while navigating through using the simple explorer type interface to get into my music folder, mp3 files will not download (server error) or stream. However, the few wma files I have stream quickly and flawlessly. FWIW, documents download with no problems or server errors. My initial infatuation with Pogoplug (and corresponding recommendations to friends) are fading fast in the last 6 months as frustrations are beginning to trump usefulness.
Having found that my MP3's encoded @ 320mpbs take well over 2 minutes to start streaming, I came accross some songs on my pc that I had were WMA format. I started streaming them on my HTC Desire and to my surprise they began playing within 5 seconds. Admittedly they were encoded @ 192kbps, but should it really make that much difference as to the time it takes to begin streaming? Is WMA the preferred format for the Pogoplug? Surely Not, it would have been mentioned before wouldn't it?
Pete F,
Have you recently updated the app? The latest app/update from the last couple of months have been truly awful. I first reported issues a year ago and over those months it had become very good and stable on my HTC Desire. Since they've messed around with it, it is much worse. I can stream mp3's but WMA's don't work anymore at the moment. MP3's don't have any album art either now, whereas previously they did.

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