First Generation iPod for Windows Hell Continued

Actually I like my iPod, but I have been disappointed with the lack of digital outputs, and bugs using non compressed or WAV files, especially the difficult in "tagging" uncompressed files. (Discussed in my other threads.)

And in fairness to Apple, I also have to admit that I LOVE surfing around on iTunes! For those of you who havent tried it, you should open one browser window to Audiogon, and the other to iTunes, read recommendations from fellow Agoners, and check out the samples piped through your main stereo. I have been doing this next to my stereo using a wireless internet connection which is the most fun I have had in a while.

But here is where my difficulties have continued:

After downloading my first few tunes from iTunes and loading up my shopping cart, I was very excited to plug in my iPod and transfer some of my new files, as well as check out the fidelity of Apples "lossless" format. Well guess what?

As my iPod tried to synch to the iTunes server, it conveniently ERASED everything I had loaded onto the iPod, a bunch of albums, a zillion songs, playlists everything?!?!?!? Go figure.

Can anyone tell me the best way to use a first generation iPod with iTunes in a Windows environment? Can I download some new software or something from Apples site? Should I get rid of it and buy one of the newer version iPods? Maybe I should just call Apple tech support? Any tips and tricks greatly appreciated.

Thanks and best wishes.