I put a decent amount of work into something similar and had a fairly polished mobile app with a good number users in a few concentrated communities using it. And it was a disaster.
Anonymity plus a shared reference point of being near each other (mine was 400ft) produced either random attempts at discussion that never matured into a conversation, or focused vitriol at real people.
We ended up discontinuing the app as it was hard to overcome the double network effect (needing people you actually want to chat with, and needing them to be nearby), and the only times where it did was because of a pretty reprehensible use case.
A street over would be Walnut or Main streets, which now have a packed barcade, and a pretty solid empanada place, etc. The change even in the last two years is extremely positive, and I would have to disagree that the article greatly overstates it.
That said, past Liberty or Main certainly has some unsavory characters, but for the most part they're only dangerous to each other. I lived in that area recently and go back frequently. I never felt unsafe in the area that's experienced significant development, even late at night.
I think a lot of people who formed their opinion of OTR back in the race riots would do well to revisit and go in with an open mind. It's quite a wonderful place now
Went through the Brandery, lived in OTR for a year and a half. Ended up falling in love with that neighborhood. Truly a special place. The tech community there far exceeds expectations for a city it's size as well.