and B) really, based solely on looks, post Super Soldier Serum Steve lends himself to stereotypical ways of thinking that Steve, spending most of his life as someone completely physically different, doesn't fit.

This is one of the things I like best about Steve's character. I have a general plot-kink for any given character being assumed to be Thing A and being revealed (to one person or to many) as really being Thing B. But as a geek and an unpopular kid in school, I have a particular fondness for characters who fit this as appearing to be a part of the popular/jock kind of group really being more of a geek-type. :-)