John,
I'm not entirely clear what the benefits of true "headlessness" are on the Windows platform. It seems to me that one can always make the Squeak window quite small (to use less Display memory), then minimize it so it is out of the way. That way, if there are any errors, one can re-size the window and debug the problem.
Not if you're going to install it on any jointly used machines. Think of a Swiki web server running as a service under NT.
Headless-ness seems to make a bit more sense on a Unix box. But there, again, one could open Squeak's display as a remote X window on some other machine, just as a debugging console.
Yeah, this would be cool. Install a Swiki demon, telnet on a special port and run your debugging session remote without even letting others know that something happens right now. WHOW!
Andreas