To jailbreak or not to jailbreak, that's the $64,000 question. For me, the answer is no. I really am just a casual iPadder. For me, its not a "business productivity tool". It is 100% for entertainment. I "upgraded" form an iPod Touch to an iPad primarily to read books and everything else is a bonus. Yeah, I am a major gadget freak and there is a lot of really neat stuff I could be doing with my iPad, but I try to have a life outside of this computer stuff. I will admit that I jailbroke my iPod Touch before I put iOS4 on it and played with it for a couple of days. To be honest, nothing I saw made me say, "Wow! This is really the shiznit!" I put iOS4 on my iPod and that will most likely be the sum total of my jailbreaking experience.
There are a lot of people who say things like, "Its MY iPad and I'll be damned if Steve Jobs is going to tell me what I can and can not put on something I own!" Well I guess I am just not that a passionate about getting stuff "off-site" for my iPad.
I work on highly complex industrial machinery (on the graveyard shift) that is, of course, driven by computers. By the time I get home in the morning, fiddling with computers is usually the last thing I want to do!