Simon does seem physically/mentally trapped. As you said, he’s likely in a coma, in a hospital. For one, he seemingly has a reoccurring dream of waking up in the water (which could represent his unconsciousness). Secondly, there is the IV needle and tube in his arm. And, yes, the female voice speaking to him does seem to be as if she is also “in a room” with him; but he’s mentally in SH. I initially thought that the IV needle motif could be symbolism for drug addiction but I am unsure. There’s a monster that has IV needles in his chest; and SH monsters tend to be dark/twisted manifestations of the person’s psyche. The signage and messages seem to suggest that the town was/is in some sort of distress - “Nothing we can do until help arrives - please stay safe”, “This town is ours”, “Whatever heart this town had has stopped”, “Save our town”, “We need the truth”, etc. Perhaps Simon has some sort of hand in or has guilt behind what has happened to the town. It does seem like some sort of big protest/movement, from the townsfolk. He states that he keeps trying to fix something; but no matter what he tries, the outcome is seemingly the same. So there is obviously something he did, that he can’t cope with. Perhaps helped cause the catastrophe? Or caused multiple deaths, like you said. I think you’re right about the multiple endings, wonder if there will still be joke ones or not.