Interesting, but it seems like something prevented it form being what it could have been.
If it's already five minutes, how long was the original version? Perhaps that ambition, without the motivation, was a factor in how it turned out.
The supporting voice actors didn't seem to have the best of mics, some of the dialog was off, and the theme seemed stuffed in at the last minute. The pacing/timing also suffered, but enough on the flaws.
You did manage to film five minutes in a week, (More-or-less) giving you more time to develop a longer story.
While it was nice seeing the guy be happy with his life, $15 an hour mowing isn't that good of money.
The animation was good, and you did fairly well with hiding the fact that the inside/outside of the houses weren't on the same set. The ending was odd, and didn't really fit with the more serious realistic tone of the rest of the short.
It was decent, and a good learning experience for you.