I think you go all in when you have a window open. Sustained mediocrity doesn’t really work and will eventually leave fans disenchanted and disengaged. A roster of Cain, Moustakas, Hosmer, Finnegan, and Manaea would have certainly done better than what Kansas City threw out last year but would it have even gotten a wild card or advanced into the playoffs? Perhaps, but it seems unlikely. It’s unavoidable that run would come to an end resulting in a rebuilding phase and some bad teams. It’s bound to happen to everyone sooner or later, it seems only the Yankees and Dodgers ilk can avoid the crash and rebuild. Take your chances and go for it when the window is open because you’ll be back to the rebuild sooner (probably much sooner) than later no matter how hard you try to avoid it.