For the most part, jailbreaking your iPad doesn't really get you much anymore. It's still iOS, you still download the apps via iTunes et al. The risk is that your iPad may get bricked (i.e. rendered unusable) at some point. What jailbreaking gets you is some minor tweaks and such. Unless there is a feature that you really, really want/need IMPO, jailbreaking isn't worth it. I jailbroke my original iPhone but haven't really seen a reason to the past several years.
Here's a link you may find interesting on jailbreaks and iOS 8 -
http://www.businessinsider.com/ios-8-jailbreak-2014-6