I've used an iPod 2G, 4G, Nano and now a Touch and I've never had a single problem with the headphone jack, but I'm pretty careful with electronics in general. One of my friends has a Zune and I've played with it a bit, but I don't really like the feeling of the user interface. Depending on how important storage capacity is for you, the iPod Touch is a pleasure to use and the fact that it can do wireless internet is worth the price of admission alone.