I liked Winnipeg. How much of it was to do with the fact that we had a rather good weather there, how much was to do with the fact that we stayed with really fantastic people, and how much with the fact that we stayed at the "posh" end of the city, in the Little Italy area around Corydon, is difficult to ascertain. Our impressions of places are undoubtedly heavily influenced by such subjective and circumstantial factors and one can't try to pretend it's not so or rationalise them away.
But I still liked Winnipeg. The city, despite being spread out on this immense plain, was not entirely un-people friendly. The public transport was available and plentiful, and there were three free buses connecting different bits of the downtown area. The inhabitants (not our hosts, but pretty much everybody we met) were without a doubt the friendliest and most helpful of all places we visited in Canada (though people in Nova Scotia came close, but even they didn't volunteer help as much as Winnipegians did). There was a tremendous local pride in the city without a smugness and sense of assured self sufficiency that probably stemmed from the fact that Winnipeg is so immensely far away from anywhere, and that it has to cope with such extremes of continental weather. And Winnipeg was the first place moving west from Toronto where the accent lost the incredibly irritating American, New Yorkish twang.
They have a nice river (in fact two), some good parks and other public spaces and one of the best preserved early 20th century downtown areas in North America. They even have a still functioning (just...) grand train station, a central clasp on the line that once connected east and west of Canada and ultimately to some extent defined it as one country.
I liked Winnipeg.