The user should not be required to have a graphical interface (usually X) running to be able to figure out what's going on. You can write console Windows applications and these should not require X to be running.
easier said than done. As of today wineconsole requires a real user32 up and running (and I never tested with ttydrv as graphic driver) I however have an (n)curse backend for wineconsole (which doesn't require user32). the core part of it is ok (curse handling), what's still badly broken is how this wineconsole should attach to the unix console (which requires some more work).
A+