In the opening paragraph of your message "freedom" above, you stated that Harold's unconscious plan would be a response to trauma. I prefer to reserve that term for affective experience far above the usual range of negative affect. If you'll send me your snailmail address I'll send a copy of the latest issue of the Bulletin of the Tomkins Institute in which I discuss our use of the term script in more detail. (Sent free to members; join up, guys! Membership application under the Tomkins Institute part of BOL.)
I like your intuition that Harold sees women as fragile; this is especially interesting in that his wife is hard, tough, and controlling, giving no suggestion of frailty, while his paramour does evoke more sense of vulnerability and frailty. Harold is by far the youngest of his siblings, and his aged father closed the store a few years ago. You are quite correct that he feels great shame at getting angry, at needing help, and at begin seen as less capable than his image. Rather than drop the idea of leaving his wife once he imaged it, he thinks about leaving her all the time but cannot out of guilt for hurting his 3 sons. As far as the degree to which Marti's appearance and style linked them, I suspect that her first-date pregnancy was the major operative factor in any further association. Guilt is a powerful force in his life.