Hi Enddoc,
Thanks for the great example, I think I can see the problem and here is also a bit of info to help. We certainly need better documentation
You have switched on "startup wait" and also set "startup delay" to 4 milliseconds. "Startup wait" causes the arduino to send a debug message to visual studio letting it know you want to wait for F5 to be pressed before the arduino will start.
The arduino starts up immediately after upload so in theory it sends the F5 wait message before Visual Studio has had a chance to start the debug listening.
So the reason why no trace messages appeared is because the startup delay is 4ms and visual micro missed the F5 message. The arduino is actually waiting so no trace messages appear. You will also find that pressing F5 in visual studio will ask you if you want to stop the debug session and re-compile. Again this is because visual studio doesn't know it is supposed to be waiting for you.
When things are working and you press F5 to continue Visual Micro uses a simple system to tell the arduino to continue. You can replicate the system simply by sending the 'c' serial character using the serial window. If you do this with your current setup you should see the debugger spring to life.
It's best to leave startup delay empty so vm uses defaults which I've tested quite well (i hope). I think the defaults are 500ms, I might be wrong. Anyway, a few seconds (3000) wouldn't hurt
Actually if you are using the main upload port for debug and you have the "Startup Pause/Dtr" true (which is the default) then vm should be re-booting the arduino when it starts the debugger.
Unrelated but a good thing to do.. Switch on the DTR checkbox on the serial monitor for COM4 I notice you have entered the default upload port as the LocalDebugPort. That's okay but you can leave it empty because vm defaults to the upload port (which I can see is selected on your std vm tool bar). I suggest you clear the LocalPort property for now.
All other settings look great. I think if you clear the localPort and set the startup delay property back to 0 it should be ok. I have my fingers and toes crossed