It seems most sites like Reddit have run out of ideas and instead of leaving things alone they just shuffle things around and sell it as innovation. Same thing for Windows 10 and office 365. Lots of visual changes but under the hood it's same old.
I agree with your argument that redesigns should have a purpose, but I disagree that the argument can be applied here.
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.
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.
Craigslist is more of a, 'Go there to accomplish specific task' end point.
Reddit is more of a, 'hang out here when your bored!' type of thing.
The former just has to work and work cleanly. The latter needs to hold it's users interest over time while staying 'hip' enough to gain users from potential competitors to stay relevant overtime.
[1] https://en.wikipedia.org/wiki/List_of_most_popular_websites
I'm not sure Fark is the best example, given that their demographic seems to be middle-aged folks (or at least older than the Millennial age range). You can't really (or simply shouldn't) do sweeping design changes if your demographic is aging. Every time I wander over to that site, it becomes very clear that a lot of the users are at least a decade older than me (likely in their 40s and 50s).
If it were a tech site, that's one thing, but Fark is more of a site for just anyone. Targeting that wider demo is going to attract less tech-minded and likely less-adaptable users compared to, say, a similar site where the userbase throws around a lot of lingo.
reddit on the other hand can more or less assume that the users that stick around will figure out the new site. They're probably right, or at least not horribly wrong, and are instead banking on retaining just a majority of users, not all of them.
Visual appeal is extremely powerful, and it's valuable to virtually any product.
ex: When searching for an apartment, I always have to put a price floor in place because everything more than ~25% below market is pure spam and there's a ton of it. It wouldn't occur to the average person that they could filter a bunch of spam out by putting a lower limit on the price of the thing they're looking for, for example. So they get an even worse experience than me, and it's pretty painful to sort through even with various tricks like that in the filtering.
From what I understand, Craigslist has been losing popularity recently, and I have no doubt that the 90s feel of the site is a big contributor.
Existing users of sites may be temporarily irked by a redesign, but they can be huge for keeping the site attractive to new users. They should happen infrequently, but they have a purpose. IMO Craigslist has made a huge mistake by leaving the site unchanged for so long.
I know for a fact that Reddit suffers from this as well. They have mentioned it in lots of places, and I'm confident that's backed up by their user studies. Visual appeal has a huge effect on new users, and I'm sure that's why Reddit is doing what they are doing.