I do think the line between "it didn't work but we'll keep trying!" and "we'll keep trying but it'll never work" textually is supposed to be embedded in Orpheus but can be muddied by the positioning of his success and failures, but in terms of staging and delivery it really comes down to Hermes' last song and how we close out on Hadestown.

Mmm, that makes sense. I think because Orpheus is the one who's sparking the rebellion against Hades, the fact that he loses Eurydice and we cycle back to him meeting her again and knowing it won't work makes that bigger progress feel lost to me too? But yeah I think it depends on the staging.