One has to be cautious of jailbreaks. But you should not fear it. Pick the right software and you are on your way to maximise your iPad and iPhone. Most people think that it is illegal, it is not. There is a wider community of apps and add-Ons / extensions.
Here is an example - try surfing on the iPad on full screen and there is marked difference. Apple has rapid scroll up but not scroll down and if you are in this form on an iPad or iPhone, you will know how valuable scroll down is.
Buying pirated apps is illegal and that is a different topic.
Here is another example - trying using FaceTime on 3G . You can't. After jailbreak and an appropriate download you. After all you lots of money for it.
Ome must thank Cooleo for it. He does good once in a while and this is one and we good graphics and more importantly the right software identified to jailbreak.
Choose the wrong one and you are toast. Take a chance and see the world.