Not always, but often, making unpopular changes is precisely what the executive is being paid to do. Their job is to implement these changes, make sure that they are the one everyone gets upset with, and then take that anger with them when they leave.
This is definitely the most reasonable approach.
Though OP never actually stated that the machine can perfectly predict the future. If that’s the case, then yes, you should just take box B. But we’re not given any information about how it makes its prediction. If @[email protected] is correct in assuming it’s a 50-50, then their strategy of taking both is best. It really depends on how the machine makes its prediction.
I agree that we shouldn’t assume corruption if TheDude starts receiving any funds, but I think it would be beneficial to have clear expectations about how donations are being used. If it’s clear that excess funds go straight into TheDude’s pockets, great. Let anyone who wants to donate go for it. But I wouldn’t want anyone to donate thinking that they’re supporting server costs when they’re actually just tipping someone. Whichever way it goes, it just needs to be clear.
This is a bit of a strange question, because an amendment is just that - an amendment. You don’t list amendments in your first draft of a constitution, you list articles. Amendments are changes made to the constitution after it’s ratified.