Hi Nick,
You seem to be close and I am not exactly sure what you are missing. So, what i can do is tell you how I did it and maybe you can pattern-match off of what i did.
So, in dashboard I created a button, gave it the name hello and a trigger id of hello as well

and then i added a task that does an ogscript.debug("triggered hello button");

then i went into the window settings on dashboard and under the keyboard shortcuts I created a new command in this window and gave the shortcut "1" and had it fire a gpi trigger "hello". So when i press 1 i will have it debug the previous line in the debug output in DashBoard.


and in the debugger on the right side it does the debug.
Thats how I did it I hope that helps in getting you started. If not send me more details on what you are trying to do and maybe I can help you out more.
Mohamed.
#DashBoard