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.
Try the latest firmware update.
This site has a wealth of info on iPods - iPod Lounge. Check out the Beginner's Guide and the Articles.
Yea, check out ipod Lounge. That sucks! I orginally got into this with an iPod Mini but quicky upgraded to the 20GB unit. iTunes can be addictive. Hopefully the firmware update will help you. If not, I would highly recommend you sell your iPod on e-bay and purchase the new 4th gen iPod. They are cheaper, have longer battery life and seem to have very few issues...

Good Luck

Your problem is because you have synching enabled in itunes. If something is on your ipod, but not in itunes, it will erase it. Disable this feature. I don't know how, but check it out on I don't use itunes because it screws up id3 tags, though if all you ever use is the ipod, then there is no problem
Don't buy encrypted music from Apple!! You can only burn so many CD's and can only record and transfer to a very small number of computers. I found this out the hard way after spending $200.00 on downloads only to find out that every time I make a back up DVD of my files it takes away my number of burns per song! Do what I do use Itunes to search for new music and then buy the CD and rip it onto your computer..... This way YOU own the music not Apple!!!
I have been demoing my music to potential clients with a]Rio Nitris , but I hear the Ipod stores more. But it also costs more. Which one do you guys use?

I also saw that 1-800-Flowers is giving away a new Ipod everyday for a month. So i am hoping to win one. You can enter without purchase too, although I did by some flowers for a cutie :) The giveaway is here:
Halekai36 is a moron. The songs you buy from the iTunes Music Store are limited to playback on FIVE computers... which hasn't been a problem for me yet. You can burn songs without limit... I think it might stop you from burning the exact same playlist more than 10 times... but just change the order a bit or swap a couple songs and you'll be fine. Apple's DRM is the fairest you can reasonably expect.
hey can someone hellp me. i have and ipod the first generation one the sort of old ones, its a 20gb. What happened was i bought the ipod and tried it on my pc and it said it needed it to be formatted so i formatted it and everything got wiped out even the setting games folders and all that. i t basically does not work anymore. when i switch it on a folder error comes up and switches itself off.someone told me i needed to download a programme off the and put it on my ipod since i havnt got the CD of it.
can anyone help me. i dont know what to do.
thanks alot.
To Abz:

I too have had myriad problems with the first gen Windows version, but have got it working now.

Start all over. Delete any iPod or iTunes programs you have loaded on your computer. Reload the software from the CD that came with your iPod. Then go to the Apple iPod site and download the latest iTunes and iPod software.

If this doesn't help, try to reset your iPod by hooking it up to charger and toggling the power switch back and forth a few times. Than simultaneously hold down the Play and Menu buttons for about 5 seconds.

Hope this helps.

Any new developments on 1st generation iPod use, please?

Here is my latest hell:

My VAIO crashed and I lost most of my computer music. Well, maybe I backed it up somewhere but I dont feel like digging it out. Then, my iPod died somehow erasing most of what was on the iPod, too other than the few tunes I purchased using a previous version of iTunes.

I thought it would be easy enough to just start over, buy some new music from iTunes on my newly reformatted VAIO, and then do a new synch with the iPod.

Well, now it seems even worse:

iTunes had no problem erasing the few songs that were left on the iPod but then just got stuck and couldnt copy any of the new ones, just kept bombing out.

I hate my iPod mini and dont want to buy the Nano or whatever so if anyone has any clues, please do tell.