Sorry, but the sad truth is...Originally Posted by M4r5h4ll
This situation will not change soon. Every iOS update includes code changes and other tricks to make it hard for non-Apple products to interact with it. Apple are taking ever more steps to make the wall round their walled garden higher. They want every piece of hardware you own to have an Apple logo on it.
If you're not OK with this they are going to try and make your life difficult.
The only workarounds right now are to give in and buy a MacBook, not ideal because iTunes is unstable and every time it trashes your iPod the only solution is to reinstall the iOs and content from a backup, a process that can take hours, Mac forums are full of such tales of woe.
Or run iTunes in a virtual box - not easy, but I got it to work, again you have to deal with iTunes, which is suboptimal in device management, but very good at selling content.
Or, install OPlayer Lite, (free from the app store) and drag and drop music to the documents folder it provides - (how long Apple will allow them to keep providing this workaround is another question).
P.S. Do not update your device iOS, no matter how insistently it asks you too, this will only make things worse as far as connecting it to non-Apple hardware and software goes.
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