I've been a redditor for nearly 5 years. I'm a moderator on many subs and over time i've even been given the privilege of becoming a moderater on a subreddit with over 100k users. I've been given random reddit gold on 3 occasions (a strange revenue system for letting users know you care by paying reddit to give them some minor perks for about $5), so i think i understand the site fairly accurately.
When you move away from the large subreddits, into the niche, you realize that much of reddit is actual adults, with brains, and who aren't too busy to see news, and also have a discussion about it. I've always seen this as a problem for advertisers.
Advertisers want it one way. They want to send a message, and they want that to be the only thing said.
Take this amazing ad from thai life insurance: http://www.reddit.com/r/videos/comments/22jybg/what_does_kin...
The top comment, while jokingly so, brings up the point that this is a commercial... it's not real... it's trying to make you think a certain way on purpose. It's manipulative. Reddit breaks the 4th wall. It calls bullshit, and much of the time, it's right.
Reddit's problem is that when an ad is truly impressive, a great deal, etc., the relevant firm doesn't need to pay reddit to get attention. The users will do that for them. See dollar shave club: http://www.reddit.com/r/videos/comments/qk7xr/dollarshaveclu...
I really don't think there is much of a solution for reddit, but if i were in charge, the way i would generate revenue would be to hold the successful ads hostage. Shadow ban advertisers accounts if they don't play ball. Literally remove viral commercials, but do it quietly. It's an abuse of the system and the users know that, and i think users like me would understand. Make them pay a fee to even attempt to "go viral."
That's my 2 cents.