Every time I tried the game (using OP's described steps) I "lost all hope and quit". I thought that was the joke / funny commentary: that all paths through the game involve you ending up losing. Didn't know there was a path to actually win the game until reading the HN comments. So I kept trying it over and over doing the same steps and finally won once.

I guess that's an even funnier commentary on how it's pretty much entirely luck based.