That often is a better move than to try to keep playing a game, or going through the motions. To take the first set of analogies, let’s say we’re pretty close on our language game — it’s straight Monopoly vs house-rules Monopoly. But, I refuse to play by your house rules from the start. Maybe it’s a matter of metanarratives, or something a bit like that; I’m generally predisposed against “house rules” versions of languages. Maybe you’ve earned distrust from me in the past for a linguistic version of an Overton Window with previous house games.
And hence I don't think he would have written differently had he lived 30 years later, and seen Chomsky's work, or even had Chomsky written first. The style of the two books is, of course, different indeed. The psyche behind the Tractatus and the Investigations seems quite continuous, though, or even almost unchanged in many respects.
I also think the idea that the rules of a linguistic game, or the rules (Platonic capitalization intended) of Language as Game, with their abstraction beyond individual games, conflict with the idea of meaning as use.
I agree with the idea that the use of language is in general gamelike, and with different games in different situations. Most of the rest of Wittgenstein's thought, the older I get, the more I distance myself from it in particulars.
I've not yet talked much about Wittgenstein's theory of meaning as use, also expressed in the PI. It was, as readers of that book know, expressed in seeming opposition to Augustine's definition of meaning.
But, that's not quite right. I see Wittgenstein as attempt to reconstruct a better version of some of Augustine's ideas, rather than deconstructing them, and this reconstruction as being driven in part by Platonic thought.
Why do I say this?
I think an unspoken idea behind meaning as use parallels that of games. Sometimes we disagree. And, with the use of words, and the meaning behind them, I think Wittgenstein is hinting at Platonic ideals as the ultimate dictionary. Because grammar, sociological conventions and other such things aren't covered by Platonic theory, Wittgenstein, in talking about rules as abstract, or abstracts perhaps even more, can't hat-tip to Plato in the same way.
I think Wittgenstein related to Augustine more broadly as one tortured soul to another, including, per Wiki, via the influence of Otto Weininger. Certainly, the fact he thought Weininger wrong in an "interesting way" reflects issues with sexuality and more.