The catch is where you say "after a person knows the nikud". Most words and expressions, beginning with mundane things like road signs and people's quick handwriting, and ending with things a professional adult needs, like professional articles, do not come with nikud. Thus, there are several ways to say every word. Perhaps if there is a simpler system, and public signs use it (and, by it being simple and quick, people can write using it), it will be easier.

Actually, there are Latin languages that are even easier than Hebrew in this respect, such as Spanish, the ultimate phonetic language (except for very few words). The additional bonus is that Spanish sports five simple vowels which actually appear in every spelling of the words (as opposed to nikud which is seldom used in everyday communications).

Actually, the nikud problem is not just an issue in itself. If you add it to the fact that people learning Hebrew have to learn to use a whole new Alphabet - which has two commonly used forms (dfus and ktav) the plot thickens.

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Why of course. But firstly, many people do not handwrite in cursive, and secondly, it is not as different from print as is "ktav" from "dfus".