I love how the OP in this thread gets "respectfully disagreed" to oblivion just for complaining about an event that he - legitimately - doesn't like, while there are many people posting false infos who get upvoted.
No, chess with death does not always lead to death.
Yes, bubonic plague has an influence on it.
Yes, this supernatural event seems to be more common than the others. Since the Reaper's Due, I've seen the Demon's Spawn like 2 times, Immortality three times (2 fails) and chess with death like 10 times. And with only one victory. I play only in multiplayer by the way, so I reckon other players as well.
And no, CK2 is not more a spreadsheet game than many other games... How do you think that other strategy games work? Event chains could totally take into account the presence of the characters involved. And in fact, it's the case in various big mods, and it's also the case when you flee the Black Death by putting your character on a boat. There are also events that get cancelled when the character is found dead. This has nothing to do with how the game works, or how spreadsheet-y it is...