I think part of it is we're talking about a huge amount of space. Maryland to Ellice to Wall St to Portage is basically the same amount of space as Wolseley and West Broadway.
I wouldn't say gentrification has begun in the West End yet. Further, I think given Winnipeg's small population, economy and overall market, I don't think we experience gentrification in the way that it's written and talked about. Most of the discussion on gentrification is centered on cities of over two million people, with exceptions of course like Hamilton. In Winnipeg you might look at an area like Osborne village over a 20 year span and realize that the houses and buildings are more well maintained now then they were previously and the average income in the area has increased, but you don't get that experience of being like "woah, this used to be a hardware store and a pawn shop and now its a wine bar and shoe store".
I think it's these blocks south of St. Matthews is where it'll become more noticeable in the next 10 years. These are all in the West End:
https://www.google.com/maps/@49.8880...7i13312!8i6656
https://www.google.com/maps/@49.8875...7i13312!8i6656
And this is also in the West End but further North:
https://www.google.com/maps/@49.8945...7i13312!8i6656
https://www.google.com/maps/@49.8936...7i13312!8i6656
It's clearly a pretty diverse area in terms of income. Further, while Wolseley is getting expensive it's not prohibitively expensive and West Broadway certainly isn't either. So I think that seepage north into the West End is still a long term view of the area.
I also saw another poster mention it, but the pandemic has impacted the services that the vulnerable rely on and their struggles have become more visible, even in busier richer cities. I don't think this is a Winnipeg exclusive.
For what it's worth, going past the boarded up 7-11 is a little jarring just in how ugly it is. It also doesn't help that there is a pawn shop across the street in a building that looks like its falling apart. That being said, a couple blocks east is this bakery that is so good and if you follow them on IG they really care about the area and community:
https://www.google.com/maps/@49.8929...7i13312!8i6656
I do have a lot of hope for Ellice and the area generally. It's a great connection from a residential neighbourhood to downtown and the Exchange district. But, unless we experience some sort of economic and population "boom", I might just be a very old person before it sees any significant investment that turns it into a more "upscale" urbanish area.
I really don't think Winnipeg as a whole is regressing though. My neighbourhood, West Broadway, has seen definite improvements just in overall vibe and appearance and the commercial area around Sherbrook continues to improve in my opinion. For what it's worth, I really don't feel threatened or afraid of the people struggling in the area - I mind my own business and usually they do as well. I think there's still more that needs to be done in terms of making West Broadway, Osborne Village, Wolseley and the Exchange more urban and just nicer overall in order to bring them up to par with other urban areas in Canada, that if we start looking at the West End it'll only lead to frustration. I think all of the areas I just listed have improved over the last 5-10 years. People like to dump on OV, but I think the state of the commercial strip doesn't tell the whole story, the area is undeniably richer and seeing a lot more development then a number of years ago. The strip will respond to it.