My iPod Touch 2nd Gen is nice, but I am falling WAY behind the times with the App Store and other functions of newer iPods (most importantly, multitasking). I've used Greenpois0n in the past to successfully jailbreak the thing and install Cydia, but things don't work out the way others have told me it should. For instance, Winterboard won't install, and crashes the iPod every time I try. Certain Cydia functions won't work or install, and in the end, I've had to restore the iPod back to its original firmware (the 2nd Gen Touch iOS only goes as high as 4.2). My question is twofold: 1. Are there any tips/tricks to having a successful jailbreak on a 2nd Generation iPod Touch MC model, and 2. Is there any way to trick either the iPod, iOS, and/or iTunes into allowing me to install a newer iOS on the device? Any advice would be great!