My own reading of Wheeler's work is not that he was eccentric or overwhelmed by flights of speculative philosophical speculation. Rather, he used poetry and whimsy to point to serious open problems in physics. For example, the participatory anthropic principle is a pointer towards the ancient measurement problem discussed by Bohr and Einstein, thought about deeply even if with some flaws by von Neumann, and that many serious thinkers including Landau & Lifshitz, Dirac, Bell, Weinberg, Tsirelson have indicated to be a problem. It from bit is Wheeler's name for the programme pioneered by von Neumann, Ludwig, Piron, of deriving operational quantum mechanics from operational axioms that make common sense, and still researched today by Hardy or Chiribella and colleages, among others.
For example, how did he phrase the question leading to the discoveries of Bekenstein and Hawking? He said to imagine pouring a cup of tea into a black hole!