It turns out that searching for error codes on xbox.com won't find anything in the Support category, and instead you have to use a dedicated Error Status Code search tool cleverly hidden away on support.xbox.com.
When I attempt to watch the large HD files, I get the 69-C00D10E0 error code, which implies it is a 4 GB file limit problem, which theoretically shouldn't be an issue when streaming because FAT32's 4 GB limit isn't involved, but I guess the Xbox 360 team was too lazy to do it right.
When I attempt to watch the 3/1 High file, it plays past the original point where I got an error message, so I have no idea what was up last time. I had previously deleted the file and then redownloaded it to test again, so I guess something may have gone wrong there.
So the lesson here is "just watch the High file and you'll be fine".
This isn't about IE on the Xbox 360, this is using (what is now called) the System Video Player to watch downloaded MP4 files served up via a UPnP/DLNA MediaServer.
I've watched nearly every subscribers-only video on my Xbox 360 (minus a few TNTs and whatnot), never had any problems until the post-Seaserpent long UPFs.
The 3/1 Unprofessional Friday video cannot be played on the Xbox 360. Tested the HD version, which fails with an error message immediately, and the High version, which plays for several minutes before causing an error message.
This has happened once before, with whichever Unprofessional Friday video was delayed for a couple days because it came in over 5 GB and had to be shrunk using some kind of arcane videographer voodoo. (I forget the exact date, sorry.) Both the HD and High versions failed that time, too.
Every other video I've watched (always the HD version) has worked without problems with the Xbox 360's H.264 decoder. (Jar Times, TNTs, other UPF episodes, Random PC Games, etc.)
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