John Oliver's Last Week Tonight bought and forgave $15M of medical debt for $60k (probably deemed uncollectible) as part of a segment about the debt collection industry. And because on paper it was a bigger giveaway than Oprah's "Everybody gets a car" giveaway.
yeah, you make them an offer. I've negotiated several debts. Its easy, they usually make it clear what they are willing/able to do. I paid one at 30% and one at 50%.