I thought this reg article on error messages was brilliant. Of course it makes sense that an error message would be required for a screen buffer related exception hence the "blem wit" extract from "There is a problem with the Memory Control Block for the shell". Did windows TSR programmers of that era consider logging to files? You betcha but debugging TSR's was often a nightmare.
My favourite error message for jaw-dropping unhelpfulness is the old win32 error
Error: "The parameter is correct"