If there is a problem with the reparations idea, it is political, not practical. The pragmatic difficulties you bring up are not insuperable and from a technical point of view they are not even very hard. The ones you list are not in fact atypical, although the class would be very large. But for a number of political reasons, explained herein, I doubt whether reparations would be a good focus for organizing, even though the demand for them is defensible as a matter of justice.
It's nice, though, to have you say once again you confine your political work to what is "political realizable," although given your commitment to the Demicans, how you square that with advocay of (for example) criminal justice reform beats me. The last criminal justice reform the Dems gave us with AEDPA. The Dems have been somewhat better on affirmative action--a policy, however, that was institutionalized by Nixon, and given constitutional and statutory legitimation by Warren Burger, Lewis Powell, and Sandra Day O'Connor (authors of the key opinion in the area, and Republicans all). I really do think that your "political realizability" is capitulation. I want my gaols to be realizable too, but I don't mean by that: likely to be adopted by the House Minority in the next Congress. As someone I read once said. "Power concedes nothing without demand. It never did and it never will." But he was a Republican too . . . . .
--jks
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