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I see where you're coming from, and it does make sense in a certain way. I also am glad one thing we've removed from the discussion is the issue of the way people utilize the privilege concept. Some progressives take it too far, drink their own kool-aid and generate new oppression, some conservatives use fear of the concept, drink their own kool-aid, and generate new oppression, but neither of those facts bear on the concept which we can analyze separately. But here are some additional things I'd like you to consider:
Since we've kind of drilled past privilege into looking at social stratification itself, I have to ask: do you believe that the world is a zero-sum game? By that I mean do you think that there is always only a set amount of 'goodness,' value, utility, whatever you want to call it about the world, and that all possible social conditions merely re-arrange the location of those values in a way that doesn't change the total?
Alternatively, do you think it's possible that some arrangements of society have more or less total value than others?
Your hobo $1 scenario makes sense if the world is a zero-sum game. If being poor is bad, and having wealth is bad, then gaining or losing wealth does not alter the value of one's experience so it's credible to argue that there is no reason to do it.
Personally, I don't see the world as a zero-sum game. The value of society is epi-phenomenal, it is something that is more than the sum of its parts. Moving wealth from the wealthy to the poor doesn't merely switch who plays the role of wealthy and poor. If done correctly it can actually lift up the part of the equation that was down before while the other remains up, and thus the whole is improved.
This has actually happened across time, if you look at the growth of the total GDP of the whole planet across history. At any moment in history, there is definite and constraining scarcity, so little can be done but shift around the existing oppression tokens, perhaps improving the whole incrementally. But the long term consequences of value shifting around between different actors actually leads to gross improvements in conditions. Even assuming all the technological advances that could've happened otherwise still happened, if only the people who had money and power in 1066 (or an equivalent proportion per capita) were the ones to have money and power now, the total GDP of the world would be a tithe of what it is now, because the mere friction of that value changing hands, both in the direct form of capital and the subtle form of power and privilege spreads the 'heat' of value throughout the medium.
To get out of the abstract into the specific; yeah, if someone ham-fistedly tries to call someone out on privilege and is an ass and just makes a scene, probably all they've done is increase the total oppression in the world, because they made the other person feel oppressed and did nothing to minimize the initial offense. Zero-sum game (actually potentially negative-sum.) But if it is done with finesse, the 'offending' person might actually come to understand how not to be as oppressive while not feeling personally slighted themselves, and then the whole actually benefits -- positive-sum game.
As for the particular of Africa, that's a bit of a different ball of wax. Trying to 'fix' people by forcing them to become a mirror of yourself is of course the classic 'White Man's Burden.' It is particularly disastrous in Africa, where merely trying to copy Western style civilization onto African civilization is fraught with problems (as a simple example, Western style ultra-concentrated urban planning is a really fucking bad idea in a continent ravaged by malaria.)
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