I'm with midnight on this one.
I've never flown at Harv's, but hired three of their grads over the years. They were all fairly easy on the machine, and on my nerves.
Southern Manitoba & Saskatchewan, and adjoining NW Ontario generally make billiard tables look mountainous, so you can see weather rolling in hours in advance.
As well as gving you a wide area in which to train, Manitoba gives you a wide area in which to fly around scouting out potential employers.
A helpful note however... Arrving at Harvair's door in the middle of July would see you fighting for aircraft with the dozen or so air cadets that arrive for the summer. April through June would be easier on your nerves.