K I will be game for this, but please do not take offence as some of these cities it has been awhile.
Montreal- Dislike how I was treated just because I had a MB plate, I was given the finger way to many times and even at a service station was refused gas.
Likes, the cities history, buildings, etc are amazing.
Quebec City- Dislike ( not a thing )
Likes ( honestly compared to the people in Montreal, they were very nice, went out of their way all the time, and the history here is breathtaking. Would go again for sure.
Toronto and Area- Dislike, hate the 401 lol. And too much traffic.
Likes, it is amazing all the towers going up, IMO though, I think they are building way to fast and not planning the best for the future. But otherwise lots to see, and so nice to be on the lake.
Thunder Bay- Well I am sorry, it seems very run down when I was there, but the people were very nice, and I loved the surrounding area.
Winnipeg- Cannot comment as I live here
Brandon -City itself I like due to the Ass Valley going through it.
Regina- I dislike the fact they do not have enough Timmies, lol
I like their ( all though short ) glass towers down town.
Saskatoon: I dislike the road system, seems very unorganized.
Like, the fact they have a beautiful river running through it and have used it properly and not built up around it to ruin it.
Calgary- I dislike the fact that a lot of people are ignorant when you are downtown, not a very friendly spot, this may be due to the younger population though. But I like some of the new towers. But really I did not find Calgary to be a place I would want to visit again.
Edmonton - Over rated, and a down town that is currently ugly compared to Calgary, also the stink on the north side is unreal from the refineries.
Liked, the way they saved the Valley, it has awsome views, and so many bike and hiking trails, you can almost have a staycation their with that valley.
Vancouver- I love this city, even though it is congested, but I kinda grew up my child hood in BC so I am biased.

Victoria- Love the fact they saved most of their old downtown and it is actually vibrant, and not just a collection of old buildings. Again I am biased.
I'd mention all the smaller cities, but I never stayed in them long enough to mention good or bad. And I have yet to get to the East coast which I want to.