I've had my iPod Classic for over four years now and there's not a hitch with it. Even the battery life is still fairly decent. I wouldn't give much of a toss though if it crapped out because I didn't pay a penny for it. I'm not entirely sure what to make of Apple products. Something about the whole grey metallic construct of Apple products in recent years seems cold and soulless and the software seems pretty much the same.
I'm using a Mac Mini most of the time in work to develop iPhone and iPad apps (yeah I'm a hypocrite), I find OS X to be a very awkward operating system and the Apple keyboards themselves are a nightmare to use. One of my biggest problems with Apple software is that it is so closed and restrictive, you even have to get a license from Apple just to test a simple software program on an Apple device. Android is open-source and there's so much you can do with Android devices and they're way more fun to use. Then again an Android device is far more likely to get fucked up from dodgy software than an Apple device so their restrictions do have a purpose.
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