I loved having the debugger separated out onto its own screen, even if it was a monochrome screen showing a bunch of tiled windows drawn with CP437 text-mode characters. To this day I miss the perfection of that setup.
One of the first times I had to use a "modern" 32-bit debugger, one with its own top-level window on the normal desktop, I was trying to find a bug triggered by focus events. Every time I hit a breakpoint, the focus would change to the debugger, dropping another focus event into the event queue, which would naturally trigger the breakpoint again once I stopped single-stepping. Having the debugger embedded in the system you're trying to debug can be very, very annoying.
One of the first times I had to use a "modern" 32-bit debugger, one with its own top-level window on the normal desktop, I was trying to find a bug triggered by focus events. Every time I hit a breakpoint, the focus would change to the debugger, dropping another focus event into the event queue, which would naturally trigger the breakpoint again once I stopped single-stepping. Having the debugger embedded in the system you're trying to debug can be very, very annoying.