About your middle paragraph: note that ASCII doesn't have left and right quotes; at 0x60 it has GRAVE ACCENT ` (not a left quote), and at 0x27 it has APOSTROPHE ' (not a right quote). Unfortunately for many years, fonts and terminals (like the SAIL ones you mentioned) continued to encourage abusing these characters as symmetric left- and right-quotes (as they were in some character sets pre-ASCII and even an early version of ASCII), despite their updated definitions.
See Markus Kahn's page at https://www.cl.cam.ac.uk/~mgk25/ucs/quotes.html which explains it well. (Also: the one-page documentation (plus one page implementation) of the LaTeX “upquote” package: http://mirrors.ctan.org/macros/latex/contrib/upquote/upquote... )