Have you installed the USB Networking hack? It has a builtin ssh client that you can use from luigi's terminal.
Screen is useful for its own features, such as multiple windows, copy & paste, re-attaching to disconnected sessions, etc. (no, the Kindle does not timeout tcp sessions).
After you ssh to the Kindle, then you can run bootdebian.sh. Other than a sandboxed environment to protect you from bricking the Kindle, I find that the native Kindle linux with USB Networking provides mostly the same functions and the debian environment is an unnecessary layer.