So what should we say? Had Osho attained those states that have been cataloged in the spiritual literature or was he just extremely well-read about them and nothing more? I am not able to say, unfortunately. But I imagine it is a subject which will arouse passions. LOL. Have at it...
I cannot say much since I just read a few of his books. He was a Jnana personality mainly, a wise man, maybe a Rishi in former lives. Maybe he did have some spiritual experience, but he was mainly intellectual and in a peculiarly original way as we have discussed.
My gut feeling is that at the beginning he maybe attained some of those states, then he let himself carried away by his own volcanic intellect and by the huge popularity he enjoyed. As you say, he surfed the wave of success and joked about it and maybe was the first one to be surprised about it. But then he chose not to disappoint his followers and accepted his role of 'Prophet' in a sardonic attitude.
The above is just one hypothesis and probaly only one tiny aspect of such a complex personality.