2)
Likewise, humans will usually admire the rich man, in your example, more than the poor man, because the rich man is giving a larger concrete benefit to others, but Jesus doesn't view humans the way humans tend to view humans. He has said that the poor man is the nobler, in this case, as his sacrifice is greater.
The Beatitudes were His declaration that some human virtues will be turned on their head, in the Heavenly Order.
Aristotle never heard the Beatitudes, but he can give us deep insight into the Natural Order.