Aiiiight!
Let’s see… I won’t lie: My immediate response to this was “oh no, no, no”. I had the same feeling as natashalost, Hadestown is just so smitten to its theatrical form. But, nevertheless, I wanted to interact with your ideas in a more detailed way. First though-
“No judging please. This site has too much negative mojo as it is :)”
My goal is not to judge, my goal will be to critically engage with what you brought forward.
“For information on how I would do each song (or certain moment) just ask in reply to this thread and Ill share it.”
I would echo gypsy in his advice and hope you will volunteer your ideas freely. It makes for better discussions than us having to request your ideas for each and every song.
Now, turning to the meat on the bone.
In my very personal opinion, the things that make Hadestown so intriguing are the way its stylised (very little is actually visualised, we only have visual indications of places and little physical visualisation. This, in turn, leaves a lot up to the viewer's imagination, making it so engaging.) and the way the story is structured (the influences of the old epics you have mentioned). While movies require a more literal approach due to the nature of the medium, we should refrain from spelling out too much, as this would detract from the fantastical men vs. gods setup.
I would not mind starting the movie off in a bar, wouldn’t mind Hermes taking a stage in the bar and invoking the beginning of the musical. I’d much rather have him just sing over the scenes you describe as if he is telling a story than him being actually in disguises. Hermes, although the god of tricksters, is not Aladdin’s Genie. The idea just reads to young and juvenile in character for me to fit the Hermes we are given in the text - ofc, this could change if we reconceptualise the part.
If filmed correctly and with a vision, I do think that Hadestown and the medium of film are not in irreconcilable, but it would need to be a more artistic vision that isn’t grounded in strict reality than we are used to seeing from musical films of our time. The closest I can imagine is an edgier, darker and grittier Into the Woods, as they both have that “lemme tell you a story” kinda feeling.
My mind also tends to wander towards animation with these projects. I’d love to see a imaginative concept. Just hope we wouldn’t actually see singing walls...