One is that it has be 2 500 words or less, which is actually way more difficult than it sounds. Or at least for me, as I feel like I'm just getting my story cooking when I hit the word limit. My advice is to come up with a story idea that is just a scene or snapshot of an event, because with character development and plot progression you will wrack up the words really quick. I find that for half the contest time, I'm just cutting down my story and trying to make things way more concise.
The second challenge is that you must be an Ontario resident, so if that isn't you yet, then start house shopping and making moving plans immediately.
The third challenge is the biggest one. In order to win, you need to actually write it and then send it to the Toronto Star. The biggest obstacle for many creative people is ignoring those nasty inner thoughts that are saying that you aren't good enough or what you created is garbage. Don't listen to them. You can never win if you don't ever write it and send it. As someone who struggles with self-worth and has a thousand negative inner thoughts, I promise you that you are way more talented and your story is way better than you think. I promise.
I also promise you that I will be writing a short story for the contest this year. I will try to remember to post a few short pieces over the next two months telling you how I am progressing and give a window into my creative process. Or at least, I will if I think it is interesting and worthwhile. I may at least give a word count update on how things are going when we get closer to the deadline.
For now, if you are living in Ontario, you love to write, and you've always dreamed of having a short story published then this is the contest for you. Check out this page for the all the contest details.