'Dean needs to get his priorities straightened, as does Lisa if they are even DARING to accept him back into her life (which would be the biggest mistake next to her "greatest year of my life" bullshit line).'
True, but how much you want to bet that Lisa waiting for a year for Dean (and than taking him back) is something Sera finds romantic?

'In my opinion, there was nothing real about that relationship, if you could ever call it a relationship in the first place since I'm convinced it was more of Lisa letting Dean in just to care for her son, despite that he's not exactly role model material because of his emotional baggage and fucked up psychological issues.'
True. I have wonder why Lisa would even want a guy like Dean to be a father figure; did she date nothing but real jerks before Dean came along?

'Surely Dean probably wanted stability, but again he admitted that it was all based around a lie, a falsehood. Something that isn't who he is. That is not our Dean Winchester.'
True. You could even make the argument that Dean's inability to let Ben and Lisa go stem from his (I'll never leave you) abandonment issues. For all we know Dean was attracted to Lisa and Ben and that whole life because Lisa reminded him of Mary.