Any overview, even if vetted by vast teams of international copyright lawyers, can only brush the surface of the issues. At best, you could end up with a list of reasons to eliminate certain licenses based on your personal goals, with the wordings chosen by the ideologies of the lawyers involved. Would this be any better than GitHub deciding internally which license(s) they want to promote, and putting these at the top of the list?
I think we should start to seriously consider simplifying our software licensing environment
This I can agree with. Having seen the amount of time wasted by open-source projects on licensing issues, copyright worries, and patent fears (and the resulting reinvention of the wheel) I think simplification is the way to go. Personally, I don't think this simplification can be achieved by piling more layers of abstraction on top of copyright and contracts.
Most books and papers seem to get along alright without licenses. I'd love to see "fair use" defined more broadly, but I don't think that adding additional licensing would be an improvement. Most electronic parts can be used as building blocks for whatever project you want without worrying whether one part will "contaminate" the others or "infect" the project. Music is licensed more frequently, but I don't think amateur musicians would benefit if they had to agree to terms of service before attending a concert.
Please tell me again why we want every project on GitHub to choose and stick to a license? And who is this "we", and what do "we" stand to gain?