One thing that I keep noticing and feeling as very significant is a certain vacillation in Wittgenstein's terminology. Sometimes he talks about a proposition making sense and other times about a proposition having a sense. Sometimes he changes between the two in the course of a sentence as in the following quote from the Notebooks:
[I]f a proposition is to make sense then the syntactical employment of each of its parts must be settled in advance.. must be completely settled before that proposition can have a sense!
In his later work, he seems to overcome the view that a proposition has a definite sense that the proposition connects to. Yet he never seems to diagnose or directly address this slip in terminology as a source of the problems in his earlier work. In fact, the later Wittgenstein is also sometimes inconsistent with how he talks about 'sense'. Yet when he is trying to highlight mistakes in this area, he is (and perhaps without realising) does stick to talking about making sense:
“You understand this expression, don’t you? Well then- I am using it in the sense you are familiar with.”- As if the sense were an atmosphere accompanying the word, which it carried into every kind of application.// …he should ask himself in what special circumstances this sentence is actually used. There it does make sense.
But why the temptation to slip from one to the other? Why not only talk about a proposition making sense? Even in the quote from PI above he seems to talk about 'the sense' of a sentence (or at least a sentence as used in that context). And if we do need to talk about the sense a sentence makes,or the sense that the sentence 'has', wherein lies the false conception earlier?
In PG he writes:
On hearing the assertion “This sentence makes sense” you cannot really ask “what sense?”
Yet, of course this is a question he asks both early and late. A word doesn't by right mean this, that or the other. It is only because it used in this sense or that. The precise philosophical task (which can be done in the right way or otherwise) depends on explicating in what sense the word is used, and that determines the meaning of the word.
I will write more on this and try to work out where the arguments meet. I think it is exceptionally important as it gives a way into diagnosing where the earlier Wittgenstein went wrong, without simply assuming he was being dogmatic. It is one that if he was wrong, it was at a specific point he did so and was a subtle and understandable mistake in the context of a shared goal. Both were trying to elucidate the sense of a proposition, but something led the earlier Wittgenstein to look in the wrong place for such an elucidation.