The Wall Street Journal seems to be making its paywall work. I think the New York Times's semi-paywall is doing OK, but that's more to do with the massive surge in readers it gained after ramping up its attacks on Trump after the 2016 election.
In specialty publications, The Athletic is doing well enough to hire new beat writers. Patch is making a profit with ad-driven hyperlocal news.
Otherwise, I agree that straight news publications that aren't the Times or the Journal (and maybe the Washington Post, but it also benefits from anti-Trump sentiment, even aside from the bottomless Bezos cash)—that is, without the brand name—just don't seem viable. When the brand-name publications handle national and international news, Reuters and AP handle other stuff, and Craigslist took away classifieds 20 years ago, where is the room for the average city journal? The answer that most sensible people came to years ago is "There isn't". The only other viable model seems to be ownership by a) nonprofit charities, or b) wealthy people who enjoy the attention from owning the local newspaper.