A half-baked theory
It might sound strange, but I think that much of what happens in both Hotline Miami movies is just the characters' interpretation of the events.
The best example is the battle against Biker from Jacket's perspective; many see him getting his head crushed (even though he's wearing a helmet, LOL), but from Biker's view, he takes Jacket down in seconds. However, this is still doubtful because it has never been confirmed which of the two versions is canon.
Now think about it, what if everything Jacket is experiencing is just ideas caused by the coma he fell into when he was attacked by Richter? It sounds strange, but it's just as strange as me trying to figure out which of the two Janitors is male and which is female, and whether Ash or Alex is also the female one.
Ignoring my earlier mental ramblings, it's difficult to establish a clear timeline for some events because there are contradictory parts, but that doesn't detract from the story.
Excuse the length of the text; I've been writing this since very late at night. Anyone who wants to read it, feel free to leave a comment or a joke, or whatever you like.
Now if you'll excuse me, I'm going to watch some hardcore Jacket edits until my brain rots. Have a good day/night (depending on your time zone) and long live petting chickens!