Ok, so in 1972 Azazel finds out he needs to somehow free Lilith from hell and get a 'special child' in order to free Lucifer and in 1973 Azazel makes a deal with Mary. How did Azazel in one year go from finding out he needs to find a 'special child' to making deals with the prospective parents of psychic kids? How did he know who the kids would be? And why was it that the kids would be born in 1983. Also, remember the comment about 'the other generations'. Why didn't he try to find a special kid from the earlier generations and start on the apocalypse earlier?
Let's assume something about the psychic kids specifically born in 1983 is ubber special so Azazel goes away for 10 years then comes back to drip some blood into the kids' mouths. Why? I've always been of the opinion that the kids were born with psychic abilities. Still not sure the significance of YED dripping blood into them, since Ruby specifically said that it has nothing to do with demon blood.
And again, why did YED wait 22 years before starting his game plan again? I mean, why wait until 2005? Why wait until the kids were all 22? Why not 18? Is 22 the legal age in hell or something?
So, the plan basically was to get the psychic kids to kill each other until the strongest one is left standing. That person then gets to open the gate to hell to let out Lilith and become boy king (girl queen) with all the demons bowing down to him/her because apaprently he/she is the only one who can free Lucifer? And also the only one who can kill Lilith? That means, Azazel wasn't powerful enough to kill Lilith, right?
Now I get it that Azazel liked Sammy the best, but he wasn't very careful with keeping Sam alive. In fact, Sam could have ended up dead on multipple occasions. I'm not too bothered by it because Azazel had subsitutes so I guess he wasn't too worried. Even if Sam dies, his plan is still in place. However, why the hell was Lilith trying to kill Sam if he was the only one who could free Lucifer? I mean, how many times did she try to off him in season 3? And yeah, I know they could have just played it so that Ruby could save Sam and Dean and gain their trust. However, Lilith herself really DID try to kill Sam in season 3 finale and I don't think she was pretending then. She looked downright terrified when her white light thingy didn't work on Sam at all. And then, in Monster at the end of the book she tried to stab him with the knife. So....why? If she really needed him alive since as Ruby said, it was always him, it was always all about Sam and him being the one to free Lucifer? And going back to Monster at the end of the book, why in the world would she try to seduce him and make a deal where he and Dean die? Was it just to test Sam? I think stabbing him in the face would have thrown a wrench in her plans to free Lucifer.