I just got an iPad a couple of weeks ago. I had a co-worker pull out his iPad out and immediately start talking about jailbreaking it. I have no fear of doing it, but I do realize that sometimes going beyond what the manufacturer intended ends up making your device less stable.
What I'd like to get from you guys is your favorite pros and cons for jailbreaking an iPad specifically. Will I have upgrade issues when they ship iOS 4 for it? Will it crash? What are the killer features if I do go for it?