It turns out having one incorrect character in Debugger.c will prevent the window from show at all. It will actually work with the normal syntax:
debugwindow = 1
Yeah I was a bit confused about that and tried different entries before I realized it was broken code. Something I would suggest if you ever update the release is to set these values up normally in addition to other fundamentals like the FPS lock. At least that would have saved me some headache lol.
PS. It might also be nice to have two different preset files of Start.ini and Globals, configured by you to get the most out of the engine/mod.