I had a similar sort of late-Windows phase before moving to Linux. While I don't think I knew about GeoShell, I would use shell replacements like LiteStep and various Blackbox clones. Customizing Windows and learning/comparing different UIs on the same system taught me concepts that made it an actual "light step" towards *nix. Sadly I don't have many screenshots from that time, and I've combed through boxshots to see if I posted any, but it looks like probably not. I did manage to find this one locally (probably from bbLean or bb4win):
