I'm curious as to how you'd convert it into a feature story-wise as some of theories on the directions you could take that I though of while watching it would be pretty interesting.
Anyways, a few notes/criticisms:
There were a few continuity/editing errors [albeit minor] that probably shouldn't be acceptable in a feature; things like how Oscar Bones holds the book/the kid drops the coin etc.
Visually I thought it was good but I couldn't help shake the feeling half of it was green screened. I'm not sure if its the cinematography, camera or the compression on youtube, but for a moment there I had half convinced myself those boxes where composited together and it wasn't all live action.
Anyways, story-wise, for a short it was ok, but to be perfectly honest, I was left wanting more: there was a lot of the kid looking around, but not much of Oscar Bones, who I definitely wanted to know more about. I understand that this is just a short and I would imagine that it would be more developed in the feature.
The narration is ok for the short film, but I also don't know about it's validity in a feature format. Don't get me wrong, the voicework was great [
] but I find its a better tool to drive the story by action rather than narration unless the narration is complementing the action. If the narration is the sole driving force of the action the film can be sluggish and uninteresting, especially if the characters aren't doing much [which is what I felt about this one to a fashion].
I was also confused by the garbage bag the lady had at the end. I kind of understand what it was all about, but for a second there I kind of expected the kids body to be in it; murdered by Oscar Bones [but thats just the horror movie buff in me thinking of it.] I don't think it was spelled out well enough in any case.
Anyways, the soundtrack work was great, the foley could do with a slightly better mix [that could be improved with more editing time] and I wasn't the biggest fan of the kid [but then again, he didn't do much, so maybe that had something to do with it.]
I see this story being developed further. If you forgive the terrible pun, its bare bones at the moment. Something that came to my mind was Neil Gaiman's "Neverwhere" which may be a good source of inspiration. I'm not saying to rip it off of course, but there are some elements in the story which may be of assistance to your story: the story is essentially about 'the people who fall through the cracks' in some magic underworld in London, and homeless people are essentially it's inhabitants. In any case, I wanted to see more of the world that Oscar Bones lives in.
Maybe having him take the kid on some crazy adventure through the magical world of wishes or something along those lines. Not in a creepy pedophile way though, that's a different kind of movie.
Hope it helps and sorry it took so long to watch it and give feedback! [I hope it doesn't come across as too negative either, I just believe its better in these sort of ventures to mention what didn't work more than what did, and just say 'awesome work dude, thats the best thing I've ever seen!]
Good luck with the feature work!