I though this was a really solid take by Masnick, in particular:

As numerous people are pointing out, Reddit is discovering the same thing that Twitter is also discovering: when you build a service where the value is all the free content that users provide, you’re going to run into some problems when you suddenly start acting like you “own” all that, and you feel the need to put up paywalls for access.

A site like Reddit is as heavy on user-generated content as you can get. Compared to something like Youtube where there’s plenty of incentive for corporate posts. The effective use of Reddit by advertisers is just social listening and customer engagement. Not a space where you’re going to get a lot of bang for the buck.

You cannot make money on “a place where people stand around and talk.” So what can you sell those people? Or what can you sell to people that want to connect to the people hanging out. In order to do that you have to “enshittify” the product. Cory Doctorow got it perfectly correct in his essay.