Not all console configurations can correctly render smart quotes in help() text. See the "Æ" in "superclass's" below.

When building for pydoc-topics, it would be ideal to disable smart quotes. (I'm assuming from issue31793 that this can be done in configuration, though I'm not entirely sure how - it's not clear to me from those PRs)

---

>>> help("BASICMETHODS")
Basic customization
*******************

object.__new__(cls[, ...])
...
   Typical implementations create a new instance of the class by
   invoking the superclassÆs "__new__()" method using
   "super().__new__(cls[, ...])" with appropriate arguments and then
   modifying the newly-created instance as necessary before returning
   it.

> Not all console configurations can correctly render smart quotes in 
> help() text. See the "Æ" in "superclass's" below.

That suggests to me a mismatch in encodings, rather than inability to 
render curly quotes at all. It's 2019 and surely we don't have to target 
ASCII as the lowest common denominator any more?

> mismatch in encodings

Also likely. I haven't looked into how pydoc does its rendering, but certainly Python 3.7 on Windows should be able to print regular Unicode.

Perhaps it's not going through stdout for some reason?

In my editor (VSCode) on windows it outputs correctly as a smart quote but if I write the output to a file or the console I get the "Æ" effect. A sent a PR to replace the smart quotes with escaped quotes but I wonder if we should also do a scan across everything to see if there are more smart quote instances (I'm still pretty new to the entire codebase so I can't say for sure if this is would even be necessary)

So pydoc_topics.py is an auto-generated file, which means we need to fix the generator as well if we decide to go that route.

However, I suspect there's a problem somewhere else causing the console output to not go through stdout correctly. I'm not familiar enough with how help() works to know where.