gwern comments on The order of learning things (general to specific vs. specific to general) - Less Wrong
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This seems to be both example and fact-free theorizing. And there seem to be many kinds of learning your ordering examples do not cover, for example optimal word memorization to read a corpus: http://jtauber.com/blog/2008/02/10/a_new_kind_of_graded_reader/
While it's just theory at this point, I do think that these theories (and some discussion of them) might actually lead us to something more concrete? I mean, okay, here's another way to put it: it is easier to learn through generalization or through deriving specifics from the general? It certainly might differ from person to person. But I'm sure that there are definitely some patterns involved.
Have you considered just reading the academic literature on learning and expertise rather than theorizing and depending on the kindness of knowledgeable strangers?
Here's a good start: The Cambridge Handbook of Expertise and Expert performance.