Probably a bit late for the original poster, but I had this same problem on Monkey Island 2 (quick black screen pop-up that almost immediately disappears; then nothing). Here is how I solved it:
Navigate to game directory, find goglog.ini, find the path listed in this file under "Dir0=". Navigate to this directory and find settings.ini. Change screen resolution to 640x480. Game now laucnhes.
Your post pointed me to the final solution.
I was getting the exact same problem on Monkey Island 2 (quick black screen pop-up that almost immediately disappears; then nothing) at Win10 Home x64.
I looked at the directory (shown in the goglog.ini) for the settings.ini and it was missing altogether (the directory was empty).
So, I changed the compatibility properties of the game shortcut to run in 640x480 (properties->Compatibility->Run in 640x480 screen resolution).
Right after this, the game booted up fine, and i was able to go to the in-game settings and change the resolution to my preferred one (Help and options->Settings->Video Settings->1920x1080->Apply) and save the settings.
At this point the settings.ini was created in the folder it should be in (as per goglog.ini).
Now, you can go back to the game shortcut and remove the "Run in 640x480 screen resolution" option you set previously, although you don't really need to - the game will use the in-game resolution.
Hope this helps.