Haha no you get use to the hill after a while.. Also, it gets really fun when University St is covered in snow and ice and you have to go all the way down the hill...Good times!
I would definitely recommend upper rez, it was my first choice and I don't regret it at all. Although, in my case there were fewer choices back in the day (4.5 years ago, man I feel old...). I wanted to live close to campus so it only came down to upper rez, douglas hall and new rez. Back then, RVC was female-only and McGill had not taken over the Carrefour Sherbrooke residence yet.
Douglas hall (aka Hogwarts) is nice but a bit apart from the other 3 residences on the hill (they have their own caf) so they were segregated from the rest of us who would all meet up in BMH (the round building in the middle) for our meals.
I thought you were at McGill right now.. So you're starting next September then?