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[This is mainly just more literary interpretation. You might find that boring.]
It is interesting to hear you interpret the message of Willers to be
Eddie is an earnest idealist, trying to do his best by Dagny Taggart and her company, and that trait is his doom.
My interpretation of that ending scene is that Rand thought the prime movers (Dagny, Rearden, Galt) were the ones who made things work. You had people who were honest and capable, but not great, and they too would be left in a stagnating world if the prime movers were to leave. It was to galvanise people to action - even if you're not actively trying to mooch off people, you won't be guaranteed a place in Galt's Gulch. And if you're "just average", perhaps you can do a lot more good if you find your Dagny Taggart to support and enable.
Not to say your interpretation is wrong and mine right, but I found it interesting to have two different interpretations, especially when I, too, resonated so much with Willers!
Also, I think loyalty to one's society is something that everyone in the plot shows. From memory, we see many characters (Dagny, Rearden, even Kellogg) struggling to step away from the companies they love. It takes them a lot of time (at least for the former two, as far as the reader knows) to agree to leave.
Perhaps the better question is, to whom should one be loyal? In the end Willers decides to save the company, but in doing so he decides to leave behind Dagny. If there was ever any fatal flaw to Willers (other than "not being great"), it is that he places his loyalty in his past, and not in the people he trusted. A Hufflepuff can be loyal and supportive, but they can't be loyal to everything. If the world is burning and there is a team of people who need your support, perhaps you should abandon the world - at least for a while.
Could you explain the difference (or relationship) between ontology and a utility function? Is there a reason you change between the two? And I thought ontology is more to do with what exists - would "axiology" be a better word?