As an initial response to your thoughts on language, there was an interest conversation in the play Insignificance by Terry Johnson. I heard it on Radio 4 on Saturday. Not that I have a grasp on later Wittgenstein, it might be a comment on separation of language and empiricism. (It’s a funny play: one scene has special relativity explained in 5 minutes by Marilyn Monroe.)

The Actress (Marilyn Monroe): So I try to know things, is that so wrong?
The Professor (Albert Einstein): If I told you the moon is made of cheese, would you belive me?
A: No.
P: If I told you it was made of granite?
A: Maybe.
P: If I told you I knew for certain?
A: I believe you.
P: So now you know the moon is made of granite.
A: Yes.
P: But it isn’t.
A: I only said I knew because you said you knew.
P: Precisely. But I was wrong. Knowledge is not truth. It is merely agreement. You agree with me, we agree with someone else, we all have knowledge. But we get no closer to the truth of the moon. You cannot understand by making definitions, only by turning over the possibilities; it’s called thinking. I know something I know is there are men, there are such men “I know of greed”, “I know of hate”, “I know of evil” but I do not, I will not understand these things. If I say I know, I stop thinking. But so long as I think, I come to understand, I might approach some truth.
A: This is the best conversation I ever had.

Anti Citizen One