I would argue that the disparity is strictly formal and resists intuitive understanding. It's hard not to use some formal analysis but I shall try to hide it as best I can.
A little bit of analysis tells us that in order for the two statements to exhibit disparity, we require that A and C are each false while B can be either true or false. (See TL;DR section below for details.) This means that obtaining an intuitive feel for this disparity is, in a very real sense, counterintuitive since it relies on the counterintuitive status of (false → true) being a true statement.
In order to detail my reasoning, note (again) that we have argued that A and C must be false while B can be either true or false.
In the case B is false, stringing together three false statements lacks an intuitive feel for the disparity. In addition (false → (false → false)) resolves to (false → true), which is again counter intuitive. And similarly for statement (2).
In the case B is true, then we have to apply our intuition to the conditional (A → B) as (false → true), which is again lacking intuitive feel.
So I would argue that this disparity resists intuitive understanding and that understanding is strictly formal.
TL;DR: Here are the details :
According to your own analysis, the two statements are equivalent to
- (A → B) → C ≡ (A ∧ ¬B) ∨ C
A → (B → C) ≡ ¬A ∨ ¬B ∨ C
Since C appears as a disjunct in each, if we are to achieve disparity between (1) and (2), then we must have ¬C.
Attempting to make statement (1) true will necessarily make statement (2) true since the conjunction in (1) requires ¬B be true. Therefore, we must make statement (1) false and statement (2) true: But how do we do this?
Since C is false by (3), we require (A ∧ ¬B) be false. If A is true, then we would require that B be true; but this combination would produce a contradiction, because the truth of A would make statement (2) false whereas we want (2) to be true.
Therefore we must have ¬A true. Finally, B can be either true or false in order to achieve disparity.