I loved finding the second install tutorial via startpage that said 'do not follow the instructions on this page - go over to (link here) and do that - otherwise if you do this.. (which is basically the same I just did on the first tutorial) - it could render your server unresponsive or break other things.. shorter story - make altinstall..
Anyhow all the fun with those builds, I now have multiple libressl and openssl and pythons and it still fails something and so I can't add the other things matrix-synapse that I need.
I'm leaning toward a fresh install, new domain name and starting the whole process of all the things for a couple days to see if I can get the missing parts needed.
During this time I ended up on several of the python bug report pages and could not for the life of me figure out where the 'resolved solution' was.. I saw some discussion and other tech stuff and then marked resolved.. never got to 'what resolved it' using those pages - maybe a slimmer version would of been better, maybe I just didn't know where to look.
anyhow - looking forward to more python when I get it to all work well with others the way others expect it to. Maybe this newer python and the newer debian will make the difference.