Most of the best stuff is pretty long, so keep that in mind.
Random PC Games: Phantasmagoria (easily the first choice), Ripper, Wing Commander 3, Outcast, Police Quest: SWAT, Crusader: No Remorse and maybe Daggerfall part 1.
Load Our Last Saves: Freedom Fighters, Brute Force, Psi Ops
All the Talk Radio shows, including Drew Returns from North Korea
All three parts of the Lantern Run, to see friendships deteriorate before your eyes
Breaking Brad: Doom II Part 1
Flight Club: P51 Mustang Beta
Stuff like the Holiday Nostalgiafest and Members-only SNES party are entertaining, but very long.
Jar Time videos are okay, but not really necessary viewing.
Honestly, I'd just save as much stuff to a hard drive as you can and take some time with it. There's a lot of quality content subscriber content that's been made in the past year, and 4 days might not be enough time to hit everything on the list. Lately there's been a pretty huge dropoff, though. Dwarf Fortress didn't really interest me and the Olympiad is actively boring, as far as I'm concerned.