As I'm sure you know, English spelling is also much less phonetically obvious than Italian (and I would not be surprised to learn that English is slightly grammatically more complicated than Italian, although frankly, as far as I'm concerned, any language with grammatical gender wins for difficulty), so emphasizing correct writing might be slightly harder.
You second point is absolutely correct: English spelling is a nightmare especially if you don't have any alternative phonetic system in which to represent it. My Italian wiring makes "there" and "their" two completely different words (they would be pronounced differently if read phonetically in Italian: "ther-a" and "the-eer") - English speakers don't have the luxury of a discriminating phonetical representation. By the way, this whole thread is about "grammar pedants" - but in fact we're just talking about spelling. The construction of the sentences is very rarely wrong.
On the other hand, I'm Italian. I came to understand, after a few years living in an English speaking country, that the emphasis Italians put on writing correctly (as well as on many other things - e.g. eating well, dressing decently, avoiding public drunkenness) has no correspondence in the English speaking world.
Did I annoy you enough? :)