If you want anything to appear in the Output window, it has to come from stdout. To do this, your app needs to be linked as a "console" app. Set the /SUBSYSTEM:CONSOLE flag in the project's property page, under Linker/System set the SubSystem property to CONSOLE.
Once you have your output in the window, if you include the text "Error:" it will appear as an error, or if you set "Warning:" it will appear as a warning. If your error text begins with a path/filename, followed by a line number in parenthesis, the IDE will recognize it as a "clickable" error, and navigate you automatically to the faulting line.
