Ok, I'm going to be jailbreaking a friend's iPod Touch, but I need to know the best way to go about doing it. First, can I jailbreak it on my Sony Vaio PC notebook (running Windows Vista) and still have him be able to use it on his Macbook when I'm done? I already have all the files on my notebook to do it; firmwares, ROMs for him, and QuickPwn. Not only that, but I'm completely experienced with all of the Windows programs (winSCP, QuickPwn), but have no experience with Macs. Obviously, I wouldn't sync with my iTunes Library. I would just jailbreak his Touch, SSH in some extras like ROMs, and then have him sync his library from his Macbook. Is that possible for me to do, or should I start researching the Mac equivalents of WinSCP and QuickPwn, and transfer all the files to a CD-R? Next, will he be able to sync with both Macs and PCs easily? He said that he was told that he could only sync to one or the other, and to this day has only synced with his parent's PC. Should he have any trouble syncing with both his Macbook and his parent's PC? Again, I'm not a Mac user (yet. Please Register or Log in to view images) so I don't know what's correct on this matter. Lastly, can I put jailbroken 2.1 firmware on his Touch even if it's already been updated to 2.2 firmware? Would it still just be a shift+click on Restore? I'd appreciate any advice on this!