Python GUI programming/libraries do and have always sucked. My only fond memory in that regard is Java with Swing and LWJGL. Python version/package management.

Python GUI programming/libraries do and have always sucked. My only fond memory in that regard is Java with Swing and LWJGL. Python version/package management. Python package publishing. Ubuntu is becoming more painful with every version, I remember an optimistic time where fun stuff like wobbly windows were my main concern and only a few clicks away, now I can't even drag and drop stuff within and from my desktop properly. My external microphone doesn't work. Sometimes my computer takes minutes to boot. My speakers don't work. Graphics drivers especially are a pain in the ass, everytime. The printer isn't even detected. And all this on a relatively new device. Screensharing and setting up remote access sucks, also whoever came up with the 8 character password length limit for VNC deserves a special place in hell (and probably also in the halls of fame in various intelligence agencies). Websites and OS interfaces that are designed primarily/only for smartphones/tablets, also inconsistent GUI designs, especially Windows can fuck itself in these regards Anything OAuth related can go fuck itself, I have yet to experience a single API that makes getting credentials trivial Anything audio configuration related. It should be as visually intuitive as the Blender node editor, yet it is anything but anywhere. Neural network construction and training data mangling. AutoML can't come soon enough. Many, many command line programs with completely unintuitive flags/inputs/commands but which like many things in this world will never change because of backward compatibility.