1. Ridiculous fragmentation.
2. Ridiculous pricing.

There are currently articles from two paywalled sources on the front page of HN, Bloomberg and New Yorker. Neither of them are what I consider "the news", so subscribing to only these two would not be sufficient.

The New Yorker charges $10.83 per month (obfuscated by pricing in "per week"), for rather niche content. Bloomberg charges $34.99 (!) per month - enough to cover 2-4 movie streaming services depending on subscription level.

New York Times, another approximately $13 per month (obfuscated by making even the "per week" pricing nearly impossible to find, i.e. you know they're going to make it a pain to cancel). The Washington Post? I think it would be 60 EUR (i.e. I assume they do region-based pricing) per year for the annual subscription, but they made it hard to find out what the price after the trial period would be (i.e. if I had considered paying them, I'd now be put off because I'd expect sleazy behavior).

The NYT and WP are much less bad than I actually thought, but that still means you are paying the price of a streaming service subscription, but unless you limit yourself to one source and never follow links people send you, you keep getting hit by paywalls from all the other media that you didn't subscribe to.

None of this gives me local media, where the situation is even worse. Everything aside from a few low quality sources is paywalled, and each paywall is separate, even if the newspapers belong to the same group... so if you pay for your local newspaper/edition, but the article was published in the other region's newspaper (from the same company), tough luck, pay again. The first article I found on one such site was based on a WSJ article... which, if I wanted to read it, would be another ~$10/month (don't know the US price) paywall.

The more respectable of the two major local ones offers two separate subscriptions, one for ~30 USD/month, but that only gives you some articles, and another for about $40 USD/month that actually gives you access to all of their articles. Only their weekday edition though, their sunday edition is extra.

So, to get any meaningful value (in the sense of no longer hitting paywalls every time I click a link, I'd probably have to subscribe to at least $50/month worth of subscriptions. Just doing that would be a chore in itself.

Then I'd have to sign in on every device where I actually want to read these news. So that's at least my personal phone, work phone, personal computer, work computer (sometimes people send links at work). I have free access to some media through a corporate subscription, and just the hassle of having to log in is usually enough to either find a paywall bypass or skip the article.

Then, it's really hard to convince me that their product is superior to the free alternatives. I can see the various ways that the free alternatives suck (clickbait etc.), but I've also seen the paid ones engage in different but equally infuriating practices (e.g. not getting to the point and rather blathering on for pages and pages with meaningless speculation just so readers feel like they're getting something for their money).

Also, even if you pay, many will subject you to ads and other abusive experiences (some will gladly remove that pain if you pay just a little more...)