It's the leading down a path that is the problem. Onboarding for old-school Reddit and Craigslist isn't hard. You click on a few things. You're done.
Once the idea of leading people down a path happens, then you've got a curated directed experience that conflicts with why you came there in the first place. That's what people have a problem with.
The whole thing is presumptuous, as if they know better than you why you're there.
Reddit doesn't need a sales funnel. It's owner Conde Nast does that's one problem.
The users have a very different set of expectations set long before the new owner walked in.
Prior to the big sale, which raised a lot of expectations, which may not actually be met very well at all given how users actually use Reddit,the site was self-sustaining based on gold and intra Reddit ads.
The idea of billions of page views, based on largely organic online discussion, equaling massive dollars, isn't one proven valid.
That's a problem too.
The reason it's a problem, is curating a very compelling discussion site for advertisers runs in conflict with what makes for a very compelling discussion site.
Once the idea of leading people down a path happens, then you've got a curated directed experience that conflicts with why you came there in the first place. That's what people have a problem with.
The whole thing is presumptuous, as if they know better than you why you're there.
They don't. Let's be honest about that.