Ultimately it's the value proposition, particularly with regional newspapers. I worked at a regional newspaper and their subscription price was more than the New York Times. Their subscriber base was basically all old, suburban white people who still got print newspapers. Print is still the cash cow of regionals to this day.
They had terrible technology. Stories, of course, were always presented as... stories. They were stuck in their ways. No emphasis on, like the post mentions, creating good data products - e.g. events, restaurants, weather maps, etc.
A big hurdle for newspapers is, yes, on giving away their news for free in the early days of the web - creating a certain expectation. But also their arrogance of not adapting to the times. The Charlotte Agenda was one of the only digital only profitable news publications before it got bought by Axios. They made money from a jobs board and other ideas (that I am now forgetting) that would cater to a regional audience.
News people tend to think "journalism is sacred" to the point of myopia. Their product is outdated. I read the New York Times for national news, but regional news (which is the majority of newspapers) consistently don't appeal to me. Why would I pay to read about a carjacking in a far off neighborhood? Yes, give me important stories, but also give me visuals and data and products that would fit into the "not video" segment. Even feature stories just don't have much pizzaz - who really wants to read an interview - I want to watch an interview. Give me information that can't be expressed in video and that isn't 2000 words long with long, drawn out flowery language.
Needless to say I don't work in news anymore. The people are very interesting and I'd work in news again. But at the end of the day newspapers are selling fax machines.