I just won this thing in one of those stacker arcade games. (only cost me a buck. 1st try). So I've jailbroken it using blaikrain but sometimes after making a system change and rebooting it makes me run it again. Anyway, itunes keeps telling me to upgrade the ipod. I've read that I shouldn't in places and others tell me to. I trust you guys as you have the most updated posts out of all the forums I've looked through. I have searched through the posts to try and find my answers before you flame me for not doing so. 1. Should I upgrade? 2. Can I jailbreak afterward and in a more permanent fashion? 3. What is this iO4 that I've seen posts about? 4. Since I have to tether to jailbreak every, will upgrading make it so I won't have to anymore? 5. Can I sync this thing wirelessly? 6. Can I somehow wireless tether using my blackberry to get wifi on the road? Many thanks to all those that help!