I've owned a 3Gs and now a 4s and have jailbroken both mainly for stuff like BiteSMS and iBlacklist and adding 'themed' icons and being able to resize them etc. Cosmetic stuff. Could I live without all this? Probably. Will I be jailbreaking the ipad? Nope. Mainly because it's a pain the backside to try and use apps like Sky Go when jailbroken.