So my idea is after I've connected to the network, ssh to my home server.
For SSH into a remote server you can use many apps available on the App Store. My favorite one is Prompt.
Then from my home server ssh back onto my iPad.
You can't SSH into an iOS device without jailbreaking (unless you are an Apple engineer). You would need to jailbreak first and then install the OpenSSH package from Cydia.
Or is there an even simpler solution that I'm missing?
Why do you need to SSH into your home server if you're just using it to get into the iPad? Seems like a lot of trouble, and you might need to mess around with port forwarding on the iPad's network.
SSHing into the iPad by connecting to localhost should do the trick. I assume you've jailbroken and installed all the utilities you need onto the iPad. Shouldn't be too bad as it looks like they're all open-source programs and you can recompile them if you really need to.