Looking for a critique of first piece of writing I've ever shown anyone...

Welcome brave writer. I enjoyed your first share. Just remember to write because you enjoy it and don't get discouraged. Everything you write, helps you learn how to write better. So writing a lot is the only way to improve.

I think it's Sanderson who compared it to playing a piano. No one expects a person to sit down for the first time and be a virtuoso at the piano. However we all seem to expect that we should be instantly good writers. The difference is we don't subject others to our piano practice, but because of the nature of what writing is, we have to, in order to get the feedback we need to improve.

Some suggestions

1. I think you should start with "the barracks had become shabby". It's a little more interesting. It sets up a bit of mystery right away. The reader wants to know why they have become shabby.

2. I'm not quite sure what the conflict is. You've hinted at a couple possibilities. Too much crime not enough guards. Emotional conflict - picking on poor people trying to eat. So think about what the real issue is and as you write drop hints to make that clearer.

Thank you for sharing! I actually wasn't going to get online this morning, but I was skimming reddit on my phone and I liked this enough to go and open up my laptop.

I left a couple comments on the document itself to highlight certain lines, but my most useful suggestion is probably this: if this chunk is a set up for a longer story (and it is, clearly :D), you might want to change a little bit of detail in the two criminals that the office deals with. If they both deserve to be arrested, then Roger's cynicism doesn't seem justified because the system appears to be working as correctly as it can, even though they're understaffed. Instead you could use the first man to demonstrate the fact that A) there isn't enough room anywhere to house criminals longer than overnight, and B) the economy is shit and some people are so desperate that pissing on the tax collector is about as useful as anything else. Then with the second man who stole because he was hungry, just let that hunger be the story, rather than immediately handwaving Roger's legitimate commentary by mentioning that his theft was so excessive.

You want Roger's concerns to be validated, so we're just left shrugging him off because we don't actually have any in-universe evidence that he has a reason to be more bitter than anybody else. As it is, because he's gotten mopey about two instances of totally legit arrests, he seems like less of a cynic with a moral compass and more like... well, like an alcoholic. Stealing a drink and then immediately being wrong about something looks a lot like shorthand for alcoholism.

And maybe he really is an alcoholic, but you want him to be an alcoholic with a point.

I also just started writing seriously again after a few years, not quite as many as you, but I get where your nerves are coming from. However, you shouldn't be nervous cause this was really good!

There are a few things that could be smoothed out in terms of flow in the prose, but with more drafts and editing that should be an easy fix. Reading out loud to yourself should help you catch issues with overall flow, and reading each line one at a time from the end to the beginning can help catch any issues with in the sentence.

Otherwise your characterization, your hints at the world, and your dialogue are all very good! I would agree with the suggestion to get a clearer definition of the conflict down.

Great job though!

this is a great start. the document already has a lot of technical corrections so I'm going to avoid mentioning those. personally I think you have some great lines and a great character built. I just believe you are overthink a few parts. specifically I believe you could ease up on the detail of the steps to the barracks and the sign. I learned the hard way that sometimes less is more when it comes the details.