Is it possible to prove by enumeration or other means that there cannot be a formal proof shorter than given length of a famous conjecture?
In particular, is it easy, given a formal proof of a conjecture determine that this proof is not a proof of the conjecture?
Does the difficulty depend on the conjecture in question?
It depends on what you mean by possible. Given a proof, one could theoretically list all strings shorter than the proof and check if they prove the theorem. Most of them will be gibberish, so fail to be a proof for that reason. The number of such strings is finite, so the answer would be available in a finite amount of time. For any reasonable length of proof that finite amount of time is unreasonably long, so one cannot practically do this. This argument does not depend on what is being proved, nor on the axioms being used.