Wow. That's an oldie!
I'm going to assume it's an iPad1, given it's on iOS 3.2.2....
So, the only available option you have for upgrading is to iOS 4.3.5. For the iPad1, that version can be jail broken, however, it'll have to be a
tethered jailbreak using redsn0w (IOW, you'll always have to connect it to your computer to reboot it) jail
Take a look at this thread here for more info on that:
http://www.ipadforums.net/jailbreak...tutorial-jailbreak-ipad1-redsn0w-windows.html
Regardless of your decision, you might want to think of upgrading your iOS, whether you choose to jail break or not. You're missing out on folders, multitasking, etc. But, that's just my opinion...
Good luck in your decision.
Marilyn