Hi Corky,
Given that you have shown printfs in your screen capture. I am guessing you want to see printf messages rather than "Debug" console. There is something that we have been calling debug console but it is limited to debugger messages. e.g. when target communication fails or one of the views attempts to make invalid memory request. There is a separate console for CIO (i.e. printf) messages. Both Debug and CIO consoles are dynamically created based on need. Thus unless there is something to show they do not get created. Picture below shows both consoles after they are created.
My suggestion would be to focus on your target application. It appears that the device that you are using has minimal printf support and relatively small default heap setting. Printf can use quite a bit of heap, thus it is possible that your device can't handle what you trying to print. CIO also uses a breakpoint to trigger data transfer (roughly set somewhere inside of printf function). Thus if that breakpoint setting fails then printf would not work either.
Martin