For the second version — I've moved to Electron for UI and Go binaries for actual heavy lifting. At least that one is a known pain you can Google for.
On a related note, does anyone know of a way of creating a "stand-alone binary" or installer for PySide2?
There is also some other project (fsmb? Something like that) that is focused towards packaging pyqt apps, but it requires you to adopt its framework.
Nevertheless I'm surprised to read you had to compile anything (if you don't mean using pyuic5 to generate Python classes from QtDesigner XML files) and deal with C++ while using Qt5 with Python.
I'd like to read some examples of that.
It’s trivial to add pyuic as an external tool in most iDEs anyway.
PySide2 is LGPL licensed, so more likely to be suitable for you, since it can be used without having to provide the source of your application.
Both libraries serve the same purpose of providing Qt5 bindings for Python in slightly different ways. PySide2 has become officially supported by Qt recently, and has generally been the preferred option for closed source development due to the licensing.