Secondly, we would want them to more precisely calculate the negative externalities caused by their wealth accumulation and engage in direct reparations where possible, or at least commit to contribute a significant amount to prevent further harm in the specific sector where wealth was generated.
I think you dramatically over-estimate how often it will be possible to identify and make amends to the victims. There are a few cases, e.g.
A burglar who keeps detailed records of which houses he broke into.
A lawyer who took fees from her client despite knowing their case was doomed.
A hacker who knows exactly which bitcoin wallets he hacked.
I agree it is plausible that in these cases people might have some specific duty to the victims that takes precedence over a generalized obligation of benevolence.
But far more commonly the victims are very diffuse and cannot be individually identified:
A manager at Norilsk, whose decisions caused pollution that has hurt many people… but he can’t tell exactly who or how much.
A lobbyist whose work lead to the passing of a law that benefited her firm or union, but lead to slightly higher prices for millions of ordinary people… but has little idea who specifically, or how much for each person.
The head of a human trafficking organization, which doesn’t keep records on his victims to reduce the risk of detection.
An saleswoman who is less than 100% honest about her products, but can’t tell who would have purchased them anyway even if she had been perfectly truthful.
Or the victims might have died, either as a result of the immoral behavior or just due to the passage of time:
A mercenary who kills people in an immoral war.
An abortionist.
Someone who mis-sold financial products to the very elderly decades ago.
Someone whose ancestors sold members of rival tribes into slavery, giving their tribe and descendants wealth and power through to the present day.
In these cases it is impossible to make amends in the way you seem to want to. You could try to help people who are similar to those you helped, but I’m not sure why that is relevant. If I burgle a house on Washington Avenue, but then I lose track of the victims after they leave town, I don’t see any reason why I owe other residents of Washington Avenue any specific debt—maybe some other street has poorer people who can be helped more efficiently. Helping merely similar people doesn’t do anything for the actual victims! At this point I think I should just consider this a debt I can never repay, and focus on helping the world in general.
I agree that 1. is a problem. I think you want to keep things fairly simple for the sake of transparency, which would mean you end up being e.g. unfairly positive towards leaders of asian countries with conscientious populations and strong hygiene norms. One thing you could do would be to add “which is better than other similar countries like X, Y and Z”—but then there is still some subjectivity about which peer countries to include.
I’m less concerned about 2. Even if the majority of voters are impossible to persuade, the marginal voter theorem suggests that you only need to influence a few people. And even in a state where one party has basically no chance, there is often competition at other levels. For example, if Cuomo is the Democrat nominee for New York State Governor, he will almost definitely win—but this might help a rival Democrat challenge him for that nomination.
Your project sounds like a good one… but I agree it would be very hard. Focusing on covid only seemed like a tractable smaller version.