... the "Now" isn't actually 'saying anything'. There's no assertions in the "Now" paragraph. It was the introduction of a new query to the dialogue: "How do the poor associate money with their estimates of self-worth?"
In other words; after my "Let's" gave a hypothetical scenario with specific numbers in order to demonstrate that, "Yes, statement #2 could be true", my "Now" raised the question of: "But is it actually true?"
Ok. In that case, the answer simply seems to be "yes, they will do so." At least from personal experience, people in a very low income bracket are extremely happy to move up to a slightly higher income bracket, and the barely employed look down on the unemployed homeless while the homeless with jobs consider themselves better than the homeless without jobs. I don't however know of any real data backing this up.
A article in the Atlantic, linked to by someone on the unofficial LW IRC channel caught my eye. Nothing all that new for LessWrong readers, but still it is good to see any mention of such biases in mainstream media.
I break here to comment that I don't see why we would expect this to be so given the reality of academia.