I want to bury this here (it's on my "someday try this list"). On OS X with the Fruitz of Dojo port, you can resize the Quake window with the mouse.
And thinking of that, it shouldn't be that difficult in Windows (I can think of one potential hurdle).
Barring that potential hurdle (does the OpenGL window need reinitialized ... ugh if yes), it would just be a matter of updating the 2D width and "glwidth/glheight" of the window within the engine.
Plus setting the window creation to allow resizing, reading the messages and setting a hook to limit the minimum window resizing to something like 320x200 (HUD can't go smaller than 320 width, menu can't go less than 200 height).
Rook has a preoccupation with dual monitors, personally I'd like to see dual monitor Quake, but I find it annoying that even within a single monitor you can't resize the window in windowed mode. Or just click maximize.
/Personally, I don't plan on playing with this soon. But I want to make sure I don't forget and sounds like an interesting topic.