I apologize for banging on about the railroad question, but I think the way you phrased it does an excellent job of illustrating (and has helped me isolate) why I've always vaguely uncomfortable with Utilitarianism. There is a sharp moral contrast which the question doesn't innately recognize between the patients entering into a voluntary lottery, and the forced-sacrifice of the wandering traveller.

Unbridled Utilitarianism, taken to the extreme, would mandate some form of forced Socialism. I think it was you who commented on OvercomingBias, that one of the risks associated with Cryogenics is waking up in a society where you are not permitted to auto-euthanize. Utilitarianism might argue that the utility of your own diminished suffering would be less than the utility of others people valuing your continued life.

While Utilitarianism is excellent for considering consequences, I think it's a mistake to try and raise it as a moral principle. I lean towards a somewhat Objectivist viewpoint: namely, that the first principle we ought to start with is that each person has the right to their own person and property, and that it is immoral to try and take it from them for any cause.

Following from this, let me address your third question: I'd argue that this type of wealth transfer not only undermines long-term economic develop of the African country (empirical, I could be proved wrong), not only prevents me from spending money on quality products & investing in practical businesses (once again, empirical), but that on a deeper level it undermines the individuality which I value in the human condition. Askin which produces greater happiness & material wealth, Communism or Capitalism, is an empirical question: Omega could come down and tell me that Communism will produce 10x the happiness, or 100x, or whatever. But the idea of slamming everybody into the same, mass produced box to maximize happiness utility sounds suspiciously like Orgasmium.

I don't see how you can compromise on these principles. Either each person has full ownership of themselves (so long as they don't infringe on others), or they have zero ownership. Morality (as I would define it) demands that we fight to protect others freedom, but it says nothing about ensuring their welfare. Giving something for 'free' is just another form of enslavement - even if it's only survival and dependence in exchange for a smug sense of superiority.

On a side note, you did a brilliant job of deconstructing 'morality based on empiricism.'