The warning you're seeing is telling you that you haven't assigned a default program to open this type of file (.err). To fix:
- Navigate to the directory that contains the eplusou.err file in windows explorer
- Right click the file > Open with > choose default program > select a text editor like Notepad, Notepad++, etc.
- Close OpenStudio and reopen
- Next time you click the eplusout.err file in OpenStudio, it should open with the text editor you chose
This should work for any file types with an extension. I have never figured out how to assign a default program to files with no extension (like stderr or stdout files) in Windows.