Interesting to read this post, as when building trad games I come from a similar school of design as Monte Cook.  In fact I’ve often said that the closest thing to DayTrippers out there is MCG’s The Strange, both in core conceits and mechanics, and I think I lot of the same judgments you make above could be leveled at both games.  When playing in “Auteur GM Mode” (yes that’s a word I proudly and literally use), the DayTrippers GM is supported by a shit-tonne of randomizers and a loose narrative template, but ultimately shoulders the same types of challenges.  It’s a school of design-thought thing, I suppose.  The idea that the world is not only a blank slate, but YOUR blank slate.  Monte and I are also about the same age and we both worked for Iron Crown at one time.  There’s a thread in there somewhere.