I was trying to understand conditional entropy better. The part that was confusing me exactly was the difference between $H[Y|X=x]$ vs $H[Y|X]$.
$E[Y|X=x]$ makes some sense to me intuitively because its just the average unpredictability (i.e. information) of a random variable Y given that event x has happened (though not sure if there is more to it).
I do know that the definition of $H[Y|X]$ is:
$$H[Y|X] = \sum p(x) H(Y|X =x) $$
But I was having trouble interpreting it and more importantly, understanding the exact difference between $H[Y|X=x]$ vs $H[Y|X]$.
There is some information since you don't know the value of $X$, so
$$ H[Y|X=x] \leq H[Y|X] = \sum p(X=x) H[Y|X=x] \leq H(X,Y)$$ Merely knowing that $X$ has taken some value, lowers the amount of information you learn from $Y$.
It is certainly lower than the joint entropy of $X$ and $Y$.
$$H(X,Y) = \sum p(x,y) \log p(x,y) $$
If this were conditional expectation you'd have the linearity of expectation. Knowing that $X$ takes some value doesn't change your expection.
$$ \mathbb{E}[Y|X] = \sum p(x) \mathbb{E}(Y|X =x) = \mathbb{E}[Y] $$