I'm actually pretty much finished now, I just need to re-upload the new versions back to the archive.
I'm not sure how you're planning to upload them back to the archive, but be aware that the command line tools[1] sometimes have issues with uploading larger files. I've found that the command-line tools are more reliable (supporting more retries by default) than the direct Python API.
Also, by default, archive.org will "derive" the uploaded video into a variety of different formats (this is normally a good thing, but I'm mentioning it since you might have already re-encoded them yourself and may want to avoid the system from "messing" with them). You can turn off derivation with a command line flag "--no-derive" to the "ia upload" tool (or a "queue_derive=False" parameter to internetarchive.upload() if using the Python API).
(source: I'm currently uploading thousands of local government videos, many of them 3+ hours long, to archive.org. With this many videos, I have scripts checking the hashes of uploaded videos to make sure the process worked before deleting any source files on my machine.)
Fun moment in retrospect: Someone from Blizzard demoed a preview of Diablo on the show. In the live demo, the first monster he kills drops a Book of Identify (permanent ability). Before the game shipped, they removed that item and made buying and carrying Scrolls of Identify (consumable) into a rather annoying gameplay mechanic.
Bummer, I was going to download and watch offline using a USB in my TV.
https://www.youtube.com/watch?v=iIf6leAPaEM
(He states that there's a connection between his trying to get funding for the show and a famous TV ad.)
One great thing about the show was that it covered more than Windows and DOS, the most exciting episodes to me were the ones that showed UNIX workstations
Today's computing is pretty boring by comparison. It used to take work to keep up to date with what was going on just in consumer PCs, it seemed like an entirely new system architecture was being announced every few months. In the 80s and early 90s, specialized work for various business cases often even required entirely custom hardware. The average computer just wasn't versatile enough to cover all of the use-cases.
CC, by trying to cover a broad swatch of computing, inevitably spent lots of time in these interesting areas, even if they seem kind of niche these days.
Really fascinating is that their interview and showcase desk often features "titans" of industry like Jack Tramiel demoing something alongside a small company's disheveled software engineer. Even more interesting is how the industry has completely transformed such that the ratio of suited sales guys that used to be everywhere in the public face of computing like CC are mostly gone, and replaced by those same engineers.
Now I watch them again and I actually understand (and actually have many of these computers in my collection), but I still have that same sense of marvel at looking at a new world unfolding. The microcomputer revolution was something to behold and this show captured it.
It's fun to see the interest in retrocomputing dates back to the early 80's.