Glad to hear that you are wired for family. I think a lot of us that struggle with our failed M's are like that. That is not to say that your M has failed. Talking about D, and actually filing, meeting with the lawyers (paying for the lawyers), going through the hard cold business like facts of the D, separating, moving out, etc. are a lot different.
You are right that your H is completely dreaming if he thinks the "family" will continue as it exists. D changes everything.
If I were you, I would use some tough love on your H. Being needy and loving and caring is obviously not working and will only keep him on the same path. Force him to move out, or you move out if he won't. Split up the finances, make him live with half the money (or less). Serve him with D or separation papers. Let him see you going out or dating while he babysits. It might scare him straight.