W said at the preface to one of his works that he would dedicate it to the greater glory of God, but he would be afraid of being misunderstood. Tractatus, of course, but I think that, and even the more informed gossipy reading might miss something that his mind hovered over. I'm not at all sure what this German aristocrat was about, but despite the fact that he was doing his best to dislodge Russell's certainty with every element of thought at his command (tracing from Frege to Bohme), Russell saw in him his only hope of a real protegee.
tl;dr: Not at all an expert, I've only begun to read his stuff seriously, but I don't think we can read W apodictically, but in the manner of disputation. And in every disputation, the reason for each engaging in the question might not at first be obvious.