Really really creative idea for a nat pack. Definitely didn't see that one coming, and it's nice to get that side of Vets Day, outside of just the requisite "Let's honor this uniformed man" package.
You had a lot of very creative shots. Could tell you were moving around. I wasn't a big fan of the shaky shouldered shot in the car. The window was dirty and it the shakiness didn't fit with the pack. There are ways around that. Prop the camera up on the dashboard... or maybe just don't use that shot at all.
Could have used a lot more nat breaks in it. You have a good amount but on occasion he is talking for way too long. And at one point he takes a deep breath and sighs. RIGHT after he says "I've been through all of that"... tht would have been a GREAT place to quickly insert a nat of him sighing! It injects real emotion into the story.
Outside of that I feel like you needed to make some quicker cuts. "They turn to DRUGS, they turn to ALCOHOL".... cut each time he lists off those things. However, I understand the point of the story is just to show how he is standing there waiting. If that's the emotion you're trying to convey, that he's waiting, then you need to put some longer pauses in. Maybe a few half second breaks of traffic. And don't have the truck/car nats come up so loud. A few of those were jarring especially the first one.
Great shots, good effort at making a visual story out of a homeless guy just standing there. I would have liked to see some reactions from people walking or driving by. Grab them quick with your shotgun mic. "What do you think of this guy?" "How do you feel that he's here asking for money?". Just something to break up the monotony of the same guy talking over and over.
