See, I still think that even if Ruby was one of the YED's acolytes, even if she and Lilith were in on the plan, there is still no reason to assume he would have told them everything, precisely because he did always play his cards so close to his chest. It makes sense that they might only have known the barest outline of what he intended (very John-style strategy, doling out scraps of info on a need to know basis) so that once he was dead and they were out of hell, they were left to salvage whatever they could of his plan based on incomplete understanding of it, which would mean that their strategy has not played out as he originally intended, despite ending up in much the same place, which also makes sense.

It still bugs me that if the YED always planned to break the seals to free Lucifer it lends credibility to Alistair's claims about trying to use John as the first seal, which I really, really hate. The notion fits nicely with the YED pressing John to sell his soul for Dean - and if Lilith, who controlled the crossroads demons, wasn't fully informed of the plan at that stage, that would explain why the crossroads demon was so willing to trade John for Dean in S2 (that need to know thing can backfire so easily!). I just really hate the thought of being expected to believe in badass John who never broke under torture.

*needs to think some more*