Experience with video is excellent for most people. All the complexity is hidden from the end user, unless you are trying to hack something. In the 1990s, streaming effectively didn't exist because people didn't have enough bandwidth (it was mostly dial-up), and there was very little legal offering, and the little that existed was terrible. Home video was limited too, as few people knew how to make video files suitable for online diffusion.
Piracy did pretty well, but that's because the legal experience was so terrible. But even then, you had to download obscure players and codec packs, and sourcing wasn't as easy as it is now. For reference VLC and BitTorrent released in 2001.
I'd say the user experience steadily improved and peaked in the mid-2010s. I think it is worse now, but if it is worse now, back then, it was terrible, for different reasons.