Something that finally clicked for me when watching Hadestown live,
Hades gives Orpheus the test that he himself goes through every spring.
This really solidified in my brain when I noticed that Hades gets the red flower and is connected more solidly to the other couple. While I always understood they were mirrors, somehow the trial itself and the significance of what Hades is asking Orpheus to do never really hit me until I watched it.
But I realized that what Hades might be thinking here is, well- you may judge me for losing faith in my wife over the long course of our relationship, missing her for months at a time with few others to talk to or support me. Let's see if this romantic, bleeding heart can do that, can feel the absence of his love and his community and still keep trusting her, himself, and the system.
And he can't- one of the major themes of Hadestown is that working together and building community rather than isolating yourself and hoarding wealth is better for the heart, mind, and soul. So taking away the walls and shades and Eurydice who were supporting Orpheus leads to him doubting himself and those people and ultimately looking back.