I was born and raised in Winnipeg and to the best of my knowledge there are far worse places to move to. Winnipeg has been labelled "Winterpeg" because we get cold winters, but no colder than Saskatchewan or other prairie provinces. We are also called the mosquito capital of canada, not sure why, but of the prairie provinces, Manitoba has several lakes north of Winnipeg which add to the often humid summers we would get, possibly more mosquitoes too.
There are some really excellent restaurants (here in Ottawa, most places just don't compare in my opinion), really well-priced houses, a good job market and a decent transit system.
If you have any other questions about Winnipeg, feel free to ask me.