A brief explanation - for @forresthayes and @thedavid mostly (and for future readers of this topic).
This topic was created with the intent to collect all debugging specific knowledge and future dreams from Redwood community members (core team as other developers alike). I plan to leave it (topic) open until a few years come by without any new comments 
In addition, I created a similar topic Redwood application debugging issues which is a lot more ambitious since it is not focused on collecting ideas, but rather on creating real projects (design and implementation discussions and actual coding - by all people that express interest in that subject)
Lastly, I am also working on Windows Dev and Setup: Recommendations and Best Practices, initiated by @thedavid, who responded by my mild critic (who of you guys use Windows platform in a regular fashion). That work is still unfinished (it is “hidden” here) and it was the point where I was about to write the Debugging section in the Windows development context, that made me create the two above mentioned topics
@forresthayes I am hoping that you might be equally interested in both of these projects
@thedavid please decide where these two projects would be sited (both are new and not likely to be part of the Redwood existing repos)