Pardon any stupid questions but I am new here, I know how to operate forums though. Please Register or Log in to view images So I am starting to get bored with my iPod's limited custimization capabilities, and am now interested in this "Jailbreaking" thing. But I have a few of questions. I have briefly skimmed a few threads to see if they answered my questions, but they weren't very direct. I would also greatly appreciate it if you didn't redirect me to another thread, unless it answers ALL my questions, or show me a list of rules (I can't be bothered to read them, unless I am going to be on here for a while and post lots of threads) Before I start firing off questions: I have an iPod Touch 2nd gen, 16gb, 3.0 firmware, and a lot of music and a fair bit of apps. So here we go: 1. If I jailbreak will I lose all my files (apps, music, videos, etc.)? 1a. Is there a way to get those back onto the ipod while jailbroken via itunes? —legally. 1b. Can I get all the apps I paid for back after jailbreak? 1c. Can I still pay for apps from the app store (on iPod or PC) if I want to? 2. Can I connect my iPod to iTunes? 2b. Will I lose my jailbreak firmware if I sync? If so how can I prevent that? 3. Can I still download music/videos/apps/etc. via PC iTunes or iPod iTunes app legally? 4. Should I back up all my iPod files onto a disk via itunes before the jailbreak? 5. Is there a jailbreak for the 3.0 firmware? (I think there is, I just want to make sure) 5a. Will I have to pay for the 3.0 firmware if I decide to restore? I will probably have more questions later, but for now: What are a few Pros and Cons of jailbreaking. (make sure to mention Cons, I want to be ready for anything), and if there is a Con, could you please mention how to fix it (if possible)? Well that is all for now, thanks in advanced! Picture (below?): Screenshot of the apps I paid for.