I would quote the entire first paragraph of your Dean and John section here, but it's huge so I'll just let you know this is in reference to that whole paragraph. Dean and John never appeared to have a perfect father-son relationship. Dean was unhealthily codependent on his father just like he is on Sam. He may have seen the flaws but he loved his father so much that he ignored them and pretended not to see them. He even yelled at Sam when they were younger (A Very Supernatural Christmas) for making snide comments about him because his loyalty to John surpasses anything. Even though in Dark Side of the Moon he confesses that John and Mary didn't have the perfect marriage, he in no way faults John for that. Dean in no way resents his father. There are no implications of that, there are implications that despite all the shit, Dean loves him more than anything. Dean is Michael in human form, not Lucifer. He's the loyal son, the perfect soldier. He doesn't secretly detest the father.
Skipping on down to the sections between Dean and demons ...
I don't really have a specific part of your Dean and Ruby section to crit because it's the entirety of it that rings wrong with me. Starting at where it says Meg taught him not to trust demons -- his entire hunter experience is what taught him that. His father. His life. It has nothing to do with Meg. More importantly, though, his feelings on season 4!Ruby. In I Know What You Did Last Summer, Dean straight up admits that he's glad Ruby was there for Sam to support him. If anything, he's pissed at himself for not being there and making Sam rely on a demon instead of him. But, honestly, he's grateful to her, he just didn't know how to say it because of their relationship, which is why he couldn't actually get the words out in the scene right before Uriel and Castiel show up in the barn. It becomes even worse in When The Levee Breaks when Sam chooses Ruby over him. Ruby makes Dean's abandonment issues worse and he blames her for that. He associates her with that abandonment and everything in Sam that's ever wanted something different than Dean. He blames her for tearing his family apart -- what's left of it, anyway. After Lucifer's out of his cage, he'd be happy to pin all of it on Ruby if Sam would let him because he's just bitter and hateful of the fact that she could be what Sam needed when he couldn't, and that she abused that. She hurt Sam in the worst way possible and he can't just get over that bitterness.
In your Dean/Hell/Alastair section, I noticed a lot of inconsistencies with canon. First of all, Dean spent forty years in Hell. Thirty being tortured, ten as the torturer, and I think, based on this section, that you've completely forgotten about the last ten. You seem to understand what went on in his time in Hell -- he was having his humanity carved out, he was being ripped apart in every way possible. Not just in body, but his very being. Everything he is was being ripped from him. But, what you seem to forget is that in Heaven and Hell, he tells Sam that he enjoyed torturing people for those ten years. He liked the power and the control and he liked feeling like he was good at it. This is because he had an amazing teacher in Alastair. He hates Alastair because Alastair saw what he became down there and it's a more intimate part of himself than anyone else has ever seen. He doesn't just hate him because he's a demon or because he tortured him, and it's not that he can't come to terms with what he did -- he comes to terms with that in On the Head of a Pin which is why he's capable of actually putting it to words in Heaven and Hell -- it's because Alastair saw that, created that, and understands Dean better than most people could ever dream because of it. It's a part of him that he never wanted people to see and he can't just undo it. Alastair is the reminder of everything Dean did down there and that's why he hates him, because he doesn't just see the person that tortured him, he sees all of the people that he, himself, tortured screaming at him when he looks at Alastair. It brings him right back and it reminds him what a failure he is for breaking.
Skipping on down to the sections between Dean and demons ...
I don't really have a specific part of your Dean and Ruby section to crit because it's the entirety of it that rings wrong with me. Starting at where it says Meg taught him not to trust demons -- his entire hunter experience is what taught him that. His father. His life. It has nothing to do with Meg. More importantly, though, his feelings on season 4!Ruby. In I Know What You Did Last Summer, Dean straight up admits that he's glad Ruby was there for Sam to support him. If anything, he's pissed at himself for not being there and making Sam rely on a demon instead of him. But, honestly, he's grateful to her, he just didn't know how to say it because of their relationship, which is why he couldn't actually get the words out in the scene right before Uriel and Castiel show up in the barn. It becomes even worse in When The Levee Breaks when Sam chooses Ruby over him. Ruby makes Dean's abandonment issues worse and he blames her for that. He associates her with that abandonment and everything in Sam that's ever wanted something different than Dean. He blames her for tearing his family apart -- what's left of it, anyway. After Lucifer's out of his cage, he'd be happy to pin all of it on Ruby if Sam would let him because he's just bitter and hateful of the fact that she could be what Sam needed when he couldn't, and that she abused that. She hurt Sam in the worst way possible and he can't just get over that bitterness.
In your Dean/Hell/Alastair section, I noticed a lot of inconsistencies with canon. First of all, Dean spent forty years in Hell. Thirty being tortured, ten as the torturer, and I think, based on this section, that you've completely forgotten about the last ten. You seem to understand what went on in his time in Hell -- he was having his humanity carved out, he was being ripped apart in every way possible. Not just in body, but his very being. Everything he is was being ripped from him. But, what you seem to forget is that in Heaven and Hell, he tells Sam that he enjoyed torturing people for those ten years. He liked the power and the control and he liked feeling like he was good at it. This is because he had an amazing teacher in Alastair. He hates Alastair because Alastair saw what he became down there and it's a more intimate part of himself than anyone else has ever seen. He doesn't just hate him because he's a demon or because he tortured him, and it's not that he can't come to terms with what he did -- he comes to terms with that in On the Head of a Pin which is why he's capable of actually putting it to words in Heaven and Hell -- it's because Alastair saw that, created that, and understands Dean better than most people could ever dream because of it. It's a part of him that he never wanted people to see and he can't just undo it. Alastair is the reminder of everything Dean did down there and that's why he hates him, because he doesn't just see the person that tortured him, he sees all of the people that he, himself, tortured screaming at him when he looks at Alastair. It brings him right back and it reminds him what a failure he is for breaking.
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