You could investigate whether OSMC would work for you. I use it myself and it seems to work fine for my on my rpi's.
You seem to have loads of other repositories and/or addons installed. Some of which that are known to disrupt basic Kodi functionality. And since some of them are deemed illegal by the Kodi team, support will stop here.
Also, the Retrospect was not created and thus not supported by the LibreELEC or Kodi team.
I suggest you ask contact the people at rieter.net how to solve your problem.
As the Retrospect maiin dev, I would like to comment to this. Regardeless of the fact that there are some weird add-ons installed. The error
Is a Python error caused by the SSL library that was used with these builds. So the question would be is the actual SSL library or is there a CA missing within these builds?