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I'm not sure I understand why you even have to pay an upgrade fee. I mean you ALREADY own the music. (Well, at least have rights to it - not sure how music ownership plays out with DRM). Also, I noted that it would cost me about $37 to upgrade my music. But obviously the whole catalog hasn't been upgraded because I own a LOT more DRM'ed music than this total would indicate.
I have a Blackberry and a couple Windows Mobile devices, but I don't use them to listen to music. That's why I have two iPods! So having non-DRM music isn't hugely important to me. The only real benefit that I can see to upgrading is the increased bitrate, which would make a difference. (I use Ultimate Ears Triple-Fi 10 Pros, and yes, I can hear the difference between 128 and 256). When iTunes initially offered DRM-free tracks from EMI, I did do the upgrade and I think it cost me about $17 down and even that wasn't all the music from EMI I had.
I just rebel at the thought of paying twice for the same music, even if it is only a third of the original cost.
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XBox 360 S, 16GB iPhone 4S, iPod Classic 160 GB, Dell Inspiron Mini 1018; Macs: Mac Mini 2.4 GHz 6 GB RAM; Macbook 2.0 GHz 3 GB RAM; MacBook Air 11", 24" Cinema Display
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