But for how long? I'm fairly certain that once those 300,000 loyal readers kick the bucket that The Times' digital subscription service will too.
How is 22 million regular readers (who will keep coming back and telling their friends about your articles, because they're free) worth less than 300,000 paying subscribers (who for some reason absolutely have to read what's in The Times no matter the price, and would probably have a hard time encouraging others to be so vehement).
Not to mention the types of journalists you will attract with a readership of a very small city, vs the readership of the population of New York State.
Monetarily. The ad market has only got worse since the Times made the move away from pure ad-funded pageviews, so the ability to turn those 22 million people's eyeballs into a revenue stream has become even less viable than it was when they replaced them with 300,000 paying customers.
"Not to mention the types of journalists you will attract.."
... with an engaged and interested audience who are directly paying to read what you have to say, who aren't merely being driven to your site by clickbait headlines and paid placement? I dunno, would think you'd be able to attract pretty good journalists on that basis...