§186

In §186 Wittgenstein raises the possibility (in the voice of an interlocutor) that a new intuition is needed at each step to carry out the order correctly. I'm not clear about what is meant by 'intuition' here. In §186 Wittgenstein uses 'intuition' as if it is equivalent to 'insight' (according to the Hacker/Schulte translation). Later on, in §213 Wittgenstein talks about intuition as an 'inner voice'. My dictionary says 'quick and ready insight' or 'hunch'. Is intuition also used to mean something like knowing/feeling sure but without evidence?

If intuition is an 'inner voice' is it your voice? - Presumably there are similar sceptical worries about what you mean by the words which make up your thoughts. - If there are sceptical worries about rule following then there are presumably also sceptical worries about what we mean by our words/what our words mean (because an explanation of the meaning of a word plays the role of a rule for the use of that word).

In §213 Wittgenstein scotches the suggestion that an intuition is needed at each step: "If intuition is an inner voice - how do I know how I am to follow it? And how do I know that it doesn't mislead me? For if it can guide me right, it can also guide me wrong."

In §186 it seems that Wittgenstein also wants to reject the possibility that the correct way to go on is the way that A intended:
(1) ...because if A meant for B to write '1002' after '1000' then A presumably also meant for 'B' to write '15,544' after '15,542' and '89,012,018' after '89,012,016' - but this would mean that A intended an infinity of steps at once, which is impossible.
(2) If A were to respond by saying that they didn't mean an infinity of sentences but rather they meant "that B should write the next but one number after every number that he wrote; and from this stage by stage, all those sentences follow." then it seems reasonable to respond that this is not satisfactory either - because if there are worries about '+2' then there are also worries about the sentence in italics.

This does sound as if Wittgenstein is setting up a sceptical problem. But it could be that Wittgenstein is presenting the philosophical problem in a form that those with the relevant vexations/confusions would recognise before he goes on to dissolve the problem - lay out the conceptual terrain in a surveyable representation.