Is it possible to run Squeak "headless" and open a remote window
    into the Squeak environment?

This is kind of what the pluggable web server does, eh? That might be
a starting point to consider.

-- 
Patrick Logan                 mailto:patrickl at gemstone.com
Voice 503-533-3365            Fax   503-629-8556
Gemstone Systems, Inc         http://www.gemstone.com