Should I jailbreak my iPad?
Pros:


ability to install apps not found in Apple's App Store
ability to customize the OS, UI, etc. to remove minor annoyances and trick out your iPad


Cons:


you will definitely be unable to upgrade to new versions of the OS without having to re-jailbreak
your iPad may be less stable
you can't bring your iPad in for warranty service without undoing the jailbreak
time &amp; energy: researching and performing the jailbreak, finding/installing non-App Store apps, keeping abreast of the latest jailbreak status in the face of updates, etc.


I've gone both ways depending on my needs -- my iPhone is jailbroken, my iPad is not.