This is just an absolutely wild take. Not even sure where to begin.
I mean, first off, I live part time during the year in Fort Garry, which I absolutely adore. So no "rose coloured memories" required. And you can say what you want about the city, proper, but even living just outside the city in Oak Bluff (or similar) is fabulous for the rich athletes (Buff and Doug Brown, just to name a couple...) that can afford it.
Then this take about having too many "undesirables" is just gross to even say out loud.
Now, as far as comparing Winnipeg to other markets... Winnipeg is probably most similar to Edmonton, which used to be way up there on these types of lists. Now, Edmonton is nowhere to be found. They built up the organization to the point where players actively want to be there (Connor and Leon help), and there's no reason the Jets can't do likewise.
tl/Dr - Negative impressions of the city are ignorance on the part of young players who just don't know b cause they haven't really experienced it.