Hi, maia,
Count me in the "ignore/trash" column. It sounds exactly like the kind of maudlin, self-pitying email I might have sent back in my drinking days. Reminiscing about what seemed like the good ol' days.
You know nothing has changed. Think about how peaceful it's been not hearing from him. If you open the door even a crack, he will assume it's OK to continue to communicate, and nothing good will come of that. Your observations about the state of his life, and what he needs to do to change it, will NOT be welcome, appreciated, or acted upon.
Good job resisting the impulse to reply and posting here, first.