I could watch Leonard discuss this stuff all day...it's just so interesting to me how the law intersects with technology, and how that plays out in practice.
Leonard discusses a number of interesting topics in this video. He reviews relevant parts of the text of the laws themselves, but also dives into the relevant case law, which is often overlooked in discussions with non-legal folks trying to reason about how to interpret the law.
As a programmer, I often want to argue that tools like youtube-dl are legal. I feel like the should be totally legal...streaming content comes and goes for lots of reasons, and being able to timeshift it to watch on a train or airplane feels a lot like the behavior that was determined to be legal in the Betamax decision from 1984. In this mindset, it's tempting to argue that youtube-dl is totally legal, and it's upsetting when folks come along and assert that using it is a crime.
But the sad truth is that the DMCA is really badly written, and criminalizes lots of behavior that many people would think is completely reasonable (like using youtube-dl to download videos from YouTube that are Creative Commons licensed). Understanding the current state of the law is a first step towards figuring out how to improve it.