I found that when I switched to Openbox, the windows manager was missing. If I changed to boot to Openbox, then I experienced the fun reboot experience! (BTW - Just quickly go to Tools -> Hildon -> reboot to hildon and you're ok).

grep -fe | grep openbox returned no results, this confirmed my lack of windows manager.

Ran the recommended
sh -x /usr/bin/swm.sh
from SSH and found a bunch 'o errors, such as:

Make sure you install libxpm4

In the end, I believe I figured it out:

apt-get install --reinstall python2.5

Rebooted. Could have been the reinstall of python, it may have been the installation of libxpm4. Hope this helps anyone running into problems.