I'm not paying to upgrade because I know it will cost Apple more $$$ to support my DRM tracks. I figure at some point they'll want to turn off their DRM servers and I can only hope they will have a free upgrade path to iTunes+.

What do you expect? They're letting you redownload songs that you already bought. They've sold how many million DRM tracks? So now they just turn on their servers and, without charging, let you redownload every song you've ever bought from them? That would kill their server. I doubt even iTunes could support that all at once.

The pricing helps Apple in two ways: it keeps their server going, and, by adding a charge, it discourages everybody from doing it at once, which means iTunes doesn't break. I understand your frustration, but Apple's doing a good thing by making this available. Complaining is fine, but don't act like Apple's the villain for negotiating an end to DRM in the largest store on the planet.

You're speculating about Apple throwing up prices to prevent their servers from getting "killed". Why do you think they distribute iTunes media on a CDN?

You're also being a bit presumptuous on your accusations of me thinking Apple is "Evil".

iTunes DRM does not require running a server on their end. Only subscription services require that.

How do you authorize new machines?