I think the point vlehto is trying to make is: He expected his friend, who he perceived as a "man", to have a particular kind of insight after the transition.

I think the point vlehto is trying to make is: He expected his friend, who he perceived as a "man", to have a particular kind of insight after the transition. Instead, he learned that his perception of the friend as a "man" was a projection. His friend would not have felt the need to transition if she felt she was a "man." His friend could only provide more nuanced insights, because her experience was not that of a "man" becoming a "woman."