THAT my friend is why a smart person does not buy an ipod, but a generic mp3 player.
As long as mp3 exists and usb exists, an mp3 player, no matter from when, will work.

I don’t buy tech stuff much, but I download softwares. And to tell the truth, I can see softwares, too, sometimes encounter the same problem as yours. I have to update things over and over. Take antivirus softwares for example, they keep on telling me to update them so that they can continue to detect viruses for me. Having to update so often like that is just tiring Sorry if I’m interpreting the matter wrong.

I think the reason they make you update your technology is the commercial purpose. If you buy an iPod which you can use for a long time then you won’t need to buy another again, and that means no more money for them. They make sure they can drain your money one way or another…

It isn’t wrong to want your technology to work as advertised. I’m sick of that kind of money draining too.

No, it’s not wrong to want your technology to work “as advertised” but alas, in today’s global retail environment, it’s unrealistic—nay, impossible—given the speed with which technology changes and obsolesces itself, the intense competition among sellers, and not least, the nature of advertising itself, which should always be taken with a grain of salt.

Funny. My first generation ipod that I bought back in 2001 still works fine and still syncs with my PC.

@Lightlyseared Oh, sure, rub it in. :-)

My issues started when I had to get a new computer to replace my dinosaur.

Welcome to planned obsolescence. Few things sold now are repairable (at a cost cheaper than replacement), upgradeable for long, or are compatible with the rapidly changing technology.

@GloPro so why wont the ipod work with the new computer.

Ugh. Thanks for the warning. Good to know my device will be declared obsolete when I finally replace my laptop.

Well, I can still charge it and put it on a speaker dock, so it isn’t a total loss. I just figured it would be a nice backup for my entire music library.

The last laptop I had my whole library on is pretty much done, but the music I buy on my phone keeps uploading to my computer wirelessly. I can not put those new tunes on the iPod because iTunes will only link to one or the other. I can’t put my entire library on my phone, nor do I want to, but it’s frustrating that it won’t let me put my whole library on my 20G iPod. You can only link 5 devices to each iTunes, I guess. My iPod, my first laptop, my home computer, and I go through phones like crazy. I’m not sure what to do, if anything, to keep the tunes I’m still buying on iTunes, and add them to my old iPod. It holds 20,000 songs, and I’m nowhere near that.

Wait, can you describe the exact problem you are having? Is it with iTunes the software, or iTunes the store, or with the drive you are storing your songs on (i.e., not your iPod)?

@GloPro It sounds like it is not a hardware problem at all, but a permissioning and storage location issue. Yes, iTunes allows only five devices at a time. You can go through your iTunes account and designate the five devices, and delete devices you no longer use. And for simplicity’s sake, stop buying songs on your phone, buy them on your computer and then synch your devices.