Sup. Your biggest offender is your action. examples:
"He goes to several doors doing this"
Doesn't that require a separate headers? Maybe a montage of sorts?
The next scene at home is awkward because it's one long run-on sentence. It'd be better to break it up to increase legibility. If I really want to be a nitpick, things like "adjacent to the door" are just filler words because racks are usually next to the door.
Same problem in the next scene. You have a run on sentence and use a lot of gerunds ("...bringing the plate towards him and grabbing the knife") which just make the sentence more clunky.
You don't introduce Amanda. She just starts talking. And it's weird. Why would she knock to enter the kitchen? How come he didn't know she was there - why doesn't he expect her at home? Who does he think made the lasagna? Why did she leave her lasagna dish alone? Dialogue has some grammar errors too (commas and periods to make it read better).
You just need to proofread (aloud). "He goes through three doors returns to the bike..."
Some dialogue needs to be spruced up. Lines like "I don't know if I'm gonna spend it. This isn't even mine." Not only is it on the nose, but they both know it's not his, so why does he say it?
What's with the italics "I deserve this fucking money"? How does the scene describe that? How does one act that out? You can take it out entirely.
Why is this clerk checking if five dollars is counterfeit or not? Does that ever happen?

Neither ending really does much. The first one is too ridiculous and dramatic. Who kills someone over counterfeit bills? How did the police get there so fast? If they were already after her, why did she murder someone? It makes no sense and makes the viewer more confused than caring about the protagonist's death. We don't care much about him anyway. Sure he's poor, but he says things like " it's not stealing" when it clearly is. I'll get behind a poor guy trying to get by, but he's flat-out delusional.
The seconding ending is just boring. You skip way too much from the policeman to being a hobo, that it's just confusing and unfulfilling.
I think it's because your message is essentially "don't steal, stealing is bad" which is just too simple. Combined with the fact that the story is a bit of a cliche, the story just doesn't have any weight. We've ALL had this fantasy before, so what can you do to make it stick out? I mean, he doesn't even get to spend the money, so there's no guilty pleasure aspect to it. You can do anything to the story to make it more interesting. For example, maybe Chad steals the money, and he dies as a consequence making Andrew feel real weird inside. Now that's a complicated feeling.
My best advice is to just PROOFREAD. Break up these action lines into smaller bits. It's okay to use short and simple sentences if it means conveying things more clearly. Your story has basic ideas which are good in theory(conflicted protagonist has to make a hard choice), BUT it's going to take a lot more depth and work to make it effective.

Just a funny observation: Is it five thousand dollars as in American dollars? You use British expressions like "cheers" or "you told the missus?" which Americans rarely say. So where does this take place?