Thank you all for the feedback!
It's great to know that the diploma program is credible in the industry.
Your comment jlousa addresses another concern I have, it appears (looking-in from the outside at least) that family connections are unusually important in the development industry. A student internship program would be nice, but from what I can deduce, they're extremely rare or even nonexistent in this field.
idunno, a Master's in Urban Planning is definitely something I'm also considering. Previously I was under the impression that most Urban Planning graduates ended up working for municipalities, but it's good to hear that it can lead to the private sector as well. UBC's program offers an Urban Development specialization, and people have spoken highly about planning at Ryerson as well.