If we believe the Tipitaka, Shakyamuni talked about how liberated he was, what it was like to be liberated, and how to get liberated like him, pretty much nonstop, for decades. If enlightenment makes you humble then the Buddha was a charlatan and Buddhism is bosh. (This generalizes to most religions!)
Contrapositively, if Buddhism is even moderately well-founded, then at least some truly liberated people would totally scream that out, at least under some circumstances.
I'm Eastern Orthodox Christian, so I do find some sort of speaking out to be productive. The apostles did evangelize, they worked miracles and focused on others above themselves according to the Book of Acts and epistles. But even St. Paul, in his epistles, speaks openly and humbly of his own struggles with the flesh. While he's given strength for that battle, he is meaningfully but still not completely liberated from dealing with the problems sin/temptation present. I understand that everyone who calls for me to listen to a talk could only be liberated to a partial extent. I think once a mortal is fully liberated, they will no longer need to evangelize. Kind of like how we only have sex in this world, it's something for the interim. Until the Resurrection, most if not all of our lives are a work in progress.
I also pay attention to the examples of the desert fathers, many of whom held exceptional wisdom which caused them to deliberately eschew all company, out of fear of becoming prideful by asserting spiritual/intellectual superiority and taking control of the lives of the people in the cities from which they fled.
Where you said "Fuck, I don't know! Ask someone liberated, not me.", I might say "Fiddlesticks, I don't know! Ask someone further along the path with a teaching mission, not me."
By the way I don't if you were aware or not, but this man, Father Seraphim Rose was actually a former student of Alan Watts. I find his writing helpful, personally.
I can understand how you might think that if you don't believe Jesus was the Son of God. Believing in the Miracle of Kenosis, I find that demonstrates humility beyond any words I could ever hope to type.
Well, I mean, he went around saying he was the Son of God, asking people to wash his feet, kicking moneychangers out of the temple, telling people nobody would reach the Father except through him, and so on, or so it is said. Same sort of thing as Shakyamuni saying he was enlightened, had seen the beginnings and endings of countless universes that other people (and even devas and Brahman) had misunderstood, knew the path to enlightenment and the end of suffering that others should follow, urging his followers to call him by honorifics, and so on, or so it is said. Neither one of them behaved like Paul or the desert fathers.
Except that probably most Christians think Shakyamuni was, at best, mistaken about all that stuff, and Jesus wasn't.
