See comments above from ~hughjd, ~jseliger, and myself: there's a good chance that it's regulation itself that created this particular kafka-esque situation. S

See comments above from ~hughjd, ~jseliger, and myself: there's a good chance that it's regulation itself that created this particular kafka-esque situation. State tax/regulatory authorities disfavor contractor relationships, even when clear-eyed counterparties prefer it. That's probably why the buyer does all their contracting through Upwork – it's a bigger risk to do it any other way – and also why Upwork has certain patterns-of-intense-work they must either block, or convert to the government's preferred payroll-relationship.