Still that would be more work than most people would do and you are investing much time into replicating something librarys like glfw or sfml could do in a crossplatform way already and still get something worse.
It's part of my job to investigate.
Didn't keep a log of everything I changed but the debug context is now creating properly in my Win32 example. Haven't been able to remove the auxiliary buffers but at least on the Win32 example I was able to eliminate the depth/stencil so I have the option to manually create it later for use in an FBO. Not sure what I have set up wrong with GLFW that it still creates the depth/stencil.