Reddit's data isn't that valuable (as you cannot key it back to a real human), a huge swath of their users adblock, and it has tons and tons of pornographic content which - and i do not necessarily agree with - will lower ad values. The current path to monetization Reddit is trying is making their data more valuable via more detailed user profiles and chats, essentially creating a pseudonymous social network and hoping itll take off like FB.

However, I think the real money would be for them to be more like Craigslist. Subreddits could pay to upgrade to become more feature-rich "Classified"-like pages whose posts could then be further boosted (re: upsell for ad team) across other subreddits.

Users react with hostility to forced social media / redesigns geared to ad revenues. They like new features that are actually useful and enhance the experience.