Have you used the iRiver hard drive player pictured above? I own an iRiver flash player (256MB) but found it very difficult and aggravating to use. The software interface was clunky and most jukebox programs like MusicMatch and iTunes refused to recognize it. I finally got MusicMatch to recognize it (by doing a software patch) but it was still a pain in the neck to get songs in there. I also found, to my disappointment, that protected WMA and AAC files would not play on it. Now iTunes won't play WMA files but version 4.5 and higher does at least allow you to convert WMA files into AAC files.
I did like the iRiver flash player once I got the songs on it.