Our brains are pretty adept at resolving such ambiguities through context, implicit rules of pragmatics, etc. Sentence (2) may be less syntactically ambiguous but longer range dependencies, at a certain point, run up against hard limits in our ability to keep things in short term memory.

A somewhat related example is center embedding structures, which are grammatical but usually quite difficult to parse once you get a few levels deep:

https://en.wikipedia.org/wiki/Center_embedding