I was in your same situation. I emailed a lot of prof's I did highly well in and I chose two from the list of emails. we'll see how it turns out this year but try choosing profs you know would write a great letter without knowing you (some people are good hearted) .
I can assure you, I know of at least two people currently doing exactly this.
If the means are there to get to a goal that is otherwise uncertain, there will always be people who take advantage of those means to get to their end.
I can assure you, no one who gets a medal is taking any strategy designed to maximize their grades other than picking courses that interest them with grading styles that suit them (mainly, paper vs exam courses).
what kind of accommodations? I've heard that the extra time that Osgoode offers is somewhere between 5 to 10 minutes for an hour. Is it worth it? I mean, what type of disability it tries to make up for by adding 15 minutes to a three-hour exam?