You know, if you look at the Code Geass world in general and take into account the fact that Lelouch could command the entire Collective Unconscious of Humanity, what was essentially God or the main pantheon of Gods in that world, it would actually make sense as to why he seemed to have such terrible luck. The Universe, or at the very least God or the Gods, was/were absolutely helpless against Lelouch if he managed to figure out how to command it to obey him. It was probably terrified and that's why Lelouch was a Cosmic Plaything all throughout the series. God/The Gods did everything it/they could to make Lelouch want to die so it/they would no longer have to deal with such a large threat to its/their own power.
Everything tragic that happened to Lelouch still sucks, but in this context it actually makes some sense as to why his luck absolutely sucked, even by the standards of the Code Geass world.