Since size is paramount, I'd probably fill about half of this space with NES, GB, and SNES roms and the emulators to play them as well as a few highly replayable classic PC games (CIv, SIm City, X-Com, Warcraft 2, Doom) and some small programs to edit/create images, and a small compiler and text editing tool (maybe Pascal based as another commenter suggested). The rest would be filled with a tremendous amount text books in a compressed archive, both fiction and non-fiction.
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