I'm not trying to make a 1:1 comparison between the two. They are very different cities and I'm aware of that. Historically, the Downtown Portland of the 70's is a closer match, before it got hip in the 2000s, when it was an old lumberjack backwater that had seen disinvestment, suburbanization, large urban renewal projects and the demolition of a big part of its historic waterfront in the previous decades. That was when the more grassroots movements happened which eventually built it into having more high end stores now. I happened to live there from 2020-25, so that is my personal experience in the covid years when it was a nightly target of Fox News "clutch your pearls" crime expose's and had a collapse of its foot traffic down to I think 15% of its norm. I do see how recommending some cutesy Portland BS sounds arrogant or out of touch, but thats not really the point I'm trying to make. What your city does have is 3 big event venues that are large draws that bring people downtown, but are not retaining those people as soon as the event is over because there is a lack of amenities. Then they go on social media and talk sh*t. I don't think a weekend festival is the magic bullet to fix downtown, but the city needs to do SOMETHING to improve the experience of visitors or else the negative perception is going to continue and get in the way. The optics are bad, and large investment firms care about the optics.
I live in Chicago now, so STL is an easy trip and I've made it twice already. I would like to go back this summer, but genuinely had a hard time finding things to do Downtown when I was actively looking for things to do. Even as someone who wants to spend my money in downtown, it's been a struggle and would absolutely push me to put that next visit onto the backburner for another city. That's the experience I've had, and it is clearly the experience others have had. St. Louis metro has people, in fact its metro has around 300,000 more people than the Portland Metro. It's not that there's no people to go downtown, its that they are CHOOSING not to go downtown
I live in Chicago now, so STL is an easy trip and I've made it twice already. I would like to go back this summer, but genuinely had a hard time finding things to do Downtown when I was actively looking for things to do. Even as someone who wants to spend my money in downtown, it's been a struggle and would absolutely push me to put that next visit onto the backburner for another city. That's the experience I've had, and it is clearly the experience others have had. St. Louis metro has people, in fact its metro has around 300,000 more people than the Portland Metro. It's not that there's no people to go downtown, its that they are CHOOSING not to go downtown












