Once you jailbreak the iPad, you will need to install OpenSSH from Cydia. then you can use PuTTy or some other SSH program to work wirelessly through your router to gain access to your iPad and it's file structure.
What is Jailbreaking all about, why should I jailbreak my iPad? I'm not asking now to jail break the iPad (numerous YouTube for that), what additional feature do I get after jailbreaking?