Thanks for the pointer to your work and discussion in issue16895. I was
contemplating something along those lines. I had not started down that path
first because I've only relatively recently thrashed the problem enough to
understand the issues, and second because I wasn't thrilled with the
prospect of implementing anything in microsoft's shell scripting language
(called PowerShell now yes?), which being proprietary and primitive would
discourage I would think the python community from even considering looking
at the code when the inevitable bugs appear. I was intrigued to read in the
recent replies to issue
16895 about the suggestion to bootstrap. There is a lot of history to the
merits of that approach in other languages. It is surprising to me that the
approach isn't used in python. Well I guess, given that python is C under
the skin and configure/make is well established unix idiom

My progress on this topic has been in fits and starts. It's about what I can
tolerate. The state of OpenSLL all by itself is pretty bizarre. Regardless,
I believe another fit is in my near future.  Judging by the response to your
issue there is interest and hope in getting this corner of python under
control.
I will review your configure/make solution, with luck a patch to the
devguide can be just a massive simplification. On the other hand, the
discussion of what is going on in automating the process would be useful.
The existing docs did help me decode what was going on envetually.

-m