In recent years I've really grown to despise Reddit, so I'm going to get a kick out of the angst that Redditors will feel when they gradually realize that their interests and Reddit's interests diverge.
Every interest has different levels of content. Pictures range from works of art that took hours to conceptualize, to images of a cat butt with a text overlay.
As a subreddit becomes more popular, the greatest common denominator's interests take precedence. And while you can attempt a solution by splitting the sub community, say, no text overlays, that doesn't work as well everywhere.
For example, a programming community needs to split into subs for languages, and the technical level of the articles. This makes aggregation more difficult, and ruins an information flow that would include a home for overall high quality posters-- now they have a more difficult time determining where to post, and must question whether the articles they submit meet the requirements for technical depth etc.
Even then, the process of dilution begins again as the lesser posters begin to inflate the sub communities.
That said; my Dad has a saying: "things are not as good as they used to be; and they never were"
-- Kicked one of the 2 co-founders, Cheever off, rumour has it he didn't want to go as aggressively after growth as D'Angelo & other powers wanted.
-- Widely sneered at in SV as being the company to look at if you want to know what "taking it too far with forcing growth" means. Their "sign-on to view this content" is a joke. Especially if you combine with their "Our mission is to grow and spread the world's knowledge"
Personally:
-- Their site's JS is a fucking mess. Crashes both my Chrome _as well as_ my iPhone's Safari frequently.
| "sign-on to view this content"
edit: It looks like they've fixed it so you can no longer just delete the overlay. Parts of the text are replaced by images of blurred text now. Oh well.
https://productforums.google.com/forum/#!topic/websearch/N72...
Reddit has clearly meddled with the site in the past for business reasons (e.g. the Sears thing, /r/jailbait), and the hands-off-unless-we-change-our-mind policy of the administration has led directly to extreme frustration among the site's biggest influences and moderators of larger subreddits.
The only thing that separates Reddit from Digg-2.0 at this point is that there is not yet another site for disgruntled users to migrate to.
It's something that has to happen and will happen to the best of em, and it just depends on how Reddit chooses to handle the situation.
A really great example of good monetization I think is Ultimate Guitar. The site used to be completely free and the community of musicians was and still is unparalleled on the internet. They've monetized pretty heavily over the years by offering paid tools and more features/premium-content for musicians (even making their own mobile apps for things like tuners, tabs, etc). I think it was a great way to monetize the community on top of ads. However, it benefits from having a very specific focus (music) and a very focused and passionate community which makes the process of monetization a little easier.
The problem Reddit will have I think is that the community is extremely open, unfocused, and unrestricted (as well as having multiple sub-communities). Its very user-driven so it becomes difficult to creatively monetize without infringing on their "freedoms" or "openness". For example, I think /r/iama would be a great outlet for brands to come and have a conversation with the community (for example, before a movie release). However, that subreddit is ALREADY used like that, and it's very open. Anyone (including any brand) can come in and do an AMA so any type of monetization would have to to be a complement to the community (can't monetize the community itself without killing it or pissing people off). So how can Reddit monetize without just resorting to ads and promoted content? It's a difficult question and I don't see a clear answer.
If they do decide to do stuff like "featured" posts, I think they will have to be very very careful to not clutter up the user-upvoted content and hopefully they'll work hard to make the "featured" stuff interesting to the community. They'll have to make some important decisions when monetizing and I wish them the best of luck.