Ancient Greek and Sanskrit both have complex detailed grammars that leave little room for ambiguity. The language of the Dao De Jing has a minimalistic grammar, where more has to be inferred from context.
In my experience, context dependence only becomes noticeable when you don't understand, so foreign languages always appear to require more contextual knowledge than one's mother tongue. If you actually try to use a formal grammar to generate all possible parses for a sentence, you'll notice your brain filters out a lot of nonsensical but grammatically valid interpretations.
Indeed. Canonical example:
https://en.wikipedia.org/wiki/Time_flies_like_an_arrow;_frui...
https://en.wikipedia.org/wiki/Written_vernacular_Chinese
Written Chinese today is a lot easier to understand than classical Chinese.