Getting output from Console.Write/Line() to appear in the VS Output window is a non-trivial feature. it requires debugging with the "Visual Studio Hosting Process". You'll see it back in both your build directory and TaskMgr.exe's Processes tab, it has the same name as your project but ends with "vshost.exe".
A fair amount of invisible magic happens inside the hosting process. It is a custom host for the CLR that gives the CLR different behavior from the one you normally run with. It is very poorly documented, the primary reason for its existence appears to be related to security. But one goody it takes care of is being able to redirect output written with Console.Write to the Output window.
Project + Properties, Debug tab, verify that the "Enable the Visual Studio hosting process" option is still ticked.
This is otherwise perhaps a fortunate mishap. You really ought to use Debug.Print() or Debug.Write/Line() in your code to generate diagnostic strings. It uses an entirely different way to generate output, one that doesn't depend on the hosting process. It uses the default TraceListener, one that talks to the debugger directly. The underlying winapi call is OutputDebugString(). The best features of the Debug class is that the calls you make in your code are automatically removed when you build the Release version of your program. So they don't take any overhead anymore, not the case for Console.Write. And that you can reconfigure trace listeners to generate output to, for example, a file.