*Note I am still a high school student so take my advice like a grain of salt
I understand where you're coming from. I have an older brother who had the same dilemma, and he graduated UTSG but regretted that because of my parents literally forced him to do so. He keeps saying to me and my parents that if he went where he wanted to go he would have been in med school by now if it weren't for UTSG (whether or not that is true, idk). I'm not sure how this helps but I just wanted to share this story, my parents are chinese as well and man were they stubborn (they've calmed down on me because of how my brother turned out in uni).
As for question 2:
From what I've heard UofT name is quite prestigious if you email a whole bunch small start ups during the summer you'll most likely get a reply (I've heard this from a UofT CS alumni).