Lots of earlier HOPL papers are experience writeups relevant to the
question of PL design. (For example, Alan Kay did a great history of
Smalltalk, which talks about more than just the language design itself,
and the language design was influenced by the other things.)
Separate from what's in HOPL, there are other related writeups floating
around. Most recently, I saw Kent Pitman did an interesting one on
Common Lisp standardization (you'd also want look at whatever Guy Steele
says about that, John McCarthy's HOPL on Lisp in general, and various
other Lisp people's reports):
http://www.nhplace.com/kent/Papers/cl-untold-story.html
Closer to home, there's Scheme. I don't know all that's currently
written up about Scheme history (and it's ongoing, including with RnRS
and various implementations), but most of the players are still around,
and they should probably be encouraged to write if they haven't
already. Olin Shivers wrote an account of T:
http://www.paulgraham.com/thist.html
Then there's various papers and writeups on other Lisps (Clojure, Arc,
Dylan, more researchy), which might be interesting in what they chose to
change (not just added features), and why.
Separate from PL histories, and various models of computation, I think
we start to get into human issues like linguistics and aesthetics, and I
don't think that's well-understood in PL, nor does it seem to be the
same for everyone. (For example, simply from looking at how people use
Racket syntax, put roughly, it looks like some people seem to use visual
while others seem purely verbal or mathematical; what happens when
someone from one of those categories tries to design an intuitive or
convenient language for everyone, but everyone isn't processing the
language the same way?)
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