I know this is gonna cause a bit of a stirr but its just not something I know anything about. I don't think I want to do it as I'm happy with the device as is but I am keen to hear others opinions.
It won't cause a stir. The forum fully supports jailbreaking, and provides excellent tutorials for those who want to do it. I've never felt any compelling reason to JB so my devices remain stock.
I'm sure your best answers, however, are going to come from those who jailbreak.
As Kevin said, jail breaking the iPad is perfectly fine and we have a huge sub-forum that supports it. May I suggest you take a look around that sub-forum forum and read other people's trials and tribulations with jail breaking.
As we have many threads asking about jail breaking (and what people think about it) and you now have the links, I'll close this one. Thanks for your understanding.