If you want to prove $(\neg b \lor \neg c) \to \neg a$, you could also try proving proving the equivalent $a \to (b \land c)$
(I wonder if maybe that's where the $(\neg b \lor \neg c) \to \neg a$ came from in the first place?)
Anyway, proving $a \to (b \land c)$ would seem to be a little more direct: just assume $a$, and try to prove $b \land c$ ... which would merely require you to prove $b$ and $c$ individually.
Effectively, you would have to prove $a \to b$ and $a \to c$.
Now, for each of those you could prove the contrapositive .. and note that if you have $\neg b \to \neg a$ as well as $\neg c \to \neg a$, then you have shown $(\neg b \to \neg a) \land (\neg c \to \neg a)$, which is equivalent to $(\neg b \lor \neg c) \to \neg a$
So you could say that it really doesn't matter whether you try to prove $a \to (b \land c)$ or $(\neg b \lor \neg c) \to \neg a$ .. in the end, you need to prove 2 things:
Either $a \to b$ or its contrapositive $\neg b \to \neg a$
Either $a \to c$ or its contrapositive $\neg c \to \neg a$
And note, maybe for the one the direct proof is easier/more intuitive, but for the other one the contrapositive proof is easier to think about.
Also: note that you need to show both of 1 and 2. So, when you say:
this statement [i.e. $(\neg b \lor \neg c) \to \neg a$] means that showing at least one of ¬b or ¬c is sufficient to show ¬a
you are expressing what that statement means correctly ... but in order to prove that statement, it is not sufficient to show just one of 1. and 2 ... you need to prove both, so that once you have that statement, anyone who has $\neg b$ can infer $\neg a$, and that anyone who has $\neg c$ can infer $\neg a$