Well, missunderstandings and confusion are cool as long as they turn into understanding and clarity.

Now that you told me that you have something better than an iPod it is obvious that getting an iPod isn't one of the smarter options. However, if you get one for free, I suggest you hook that up to your stereo instead.
I am currently using only Mac OS X on both my G4 and a brand new G5 (dual 2.7Ghz processor 1.25Ghz bus. 8GB of ram. It is a beast). OS X Tiger (10.4) actually features a screen reader of it's own. No additional software to install. Just hit "command+F5" when the Mac starts up and everything will be read to you. Some cool navigation modes to mess with too. Voices seem to sound good too.
On my PC I used to run ZoomText 8 which is both a magnification + Screen reader program. I liked that one a lot. It was the best of outSpoken and ZoomText put together. I also used Connect Outloud but not for long. It's navigation controls were a bit of a mess. For me anyway.
I've given up on using PCs ever since my ThinkPad had it's last hard drive crash. It was a brand new drive and wooom. Just went down one day. No reason. XP was unable to re-install so I think the drive is dead. Paying for one isn't really within my plans right now since first of all I have something better and second wife and I just had a baby, moved to a new house and bought me some toys for music. Right now I don't want to blow hundreds of dollars on something that I don't need to use. Before Tiger OS X came out new Macs didn't feature any screen reader support and since that has changed I don't really intend to go back to PC horror. I never used PCs for music anyway but even for browsing the web they were .. quircky. Especially when ZoomText just came out.
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