Lots of frustrations with iTunes...please help?

I've had my iPod for forever[it's a mini..i'm not sure how many GBs...maybe 2? 4? It holds 1,000 songs ;)], and just recently I got it working again. I reset it, because I wanted to completely start over with adding songs to it. I updated everything [iTunes and my iPod] so that everything is as current as possible. But I'm having a problem with iTunes. It only lets me add one song at a time, and goes extremely slow [I mean, slow, like 3 or 4 minutes per song]. The slowness I can deal with, but lately it's been giving me this message when I try and add songs:
Attempting to copy to the disk failed. Disk could not be read from or written to.
It does it on most of my songs, and it's getting rather annoying. Does anybody have any ideas about what's going on or how I could fix it? Also, any ideas on mkaing it run faster would be appreciated.
Thank you so much in advance!

"Disk cannot be read from or written to" error syncing iPod in iTunes.

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Alexl08
I suspect these are files downloaded from Napster, Rhapsody, Sony, Walmart, or some other online store that has WMA copy protection.
Those files will not work in iTunes.
That's why Dave was asking WHERE you got them.
To get them into iTunes, you need to burn an audio CD using Windows Media Player (or some other program that can play the files) and then, import them into iTunes.
The DRM copy protection between Apple & Windows is incompatible. That's why iTunes won't let you drag them in - it can't play them. And Windows Media Player can't play sonfs from the iTunes store.
Ah, the joys of DRM: digital rights mismanagement.
edit: if you hover your mouse over one of those files in windows explorer, the little baloon info will pop up and say
Protected:Yes
You can only drag Protected:No songs into iTunes.

Lots of frustrations with iTunes...please help?

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