I'd love to have real filesystem access as well as VLC on my iPad, but when i think about JBing, all that comes to mind is people bricking their iPhones. It sounds like JBing an iPad is fairly safe as long as you're careful about what apps you use and about installing updates. For the most part, can you eventually install most iOS updates without much risk (if you take the right steps)? Honestly, what are the biggest risks of JBing an iPad? As much as I want the benefits, I can't afford a new one if I were to do anything irreversible to this one.