20 years ago I made the observation that the whole intellectual property domain was fundamentally based around all of the individual aspects of intellectual property being cleanly and completely distinguishable from each other, e.g., this is a book, this is a song, this is a movie (which is made of this song and this script), etc. But even then it was becoming clear these categories were getting fuzzier and fuzzier and in many cases outright merging, and the categories weren't going to just go together nicely because of the various contradictory assumptions in them.
The worst then, and I think still today, is computer software, which is covered by both patents and copyright. Copyright has always covered them, in the last 20 years, patents have covered more and covered less at times, but still have always covered some of it.
I'm actually a bit surprised that I've still seen no hint of the legal system directly grappling with this problem. It just keeps getting worse. I've been keeping my eyes out but I haven't seen anything.
And this is another example; nobody wrote the copyright laws for the YouTube case. If you get down to it, you have this intricate interplay of video, audio, automated systems generating some content, automated systems checking them, an extra-judicial system for mediation where I will not say the incentives are 100% misaligned, but they are certainly nowhere near 100% aligned with what they should be, with a lot of mismatches between YouTube, the copyright holders, and the video producers in terms of powers and responsibility (that is, there are many places in the system where there is power without responsibility, and responsibility without power), and we're trying to adjudicate it on 20th century law that was already, at times, kinda cobbled together. (Don't look, but we're already 1/5th of the way into the 21st century.) It's madness.