I don't really understand why they're so against doing proper advertising, so much so that they're willing to operate at a loss. Digg didn't fail because of advertising and if reddit can approach advertising in a "mature" way -- not just going after every penny -- it could work out well.

    you come under editorial pressure from advertisers to 
    remove or modify it…This eventually results in a 
    watering down of the true, authentic content on the site

If you're in a situation where you have no advertising and you're losing money, why not be in a situation where you have some advertising and if an advertiser gets annoyed you tell them to leave and not work with you again? If reddit has value to advertisers a few annoyed advertisers aren't going to break the site, especially when it can exist as a money losing business.

Their current advertising is just... pointless, I rarely see adverts on reddit, almost every page load has the advertisement block filled with an internal reddit notice (eg: "check out the FAQ!", "Thanks for not using adblock", "check out reddit gifts") or an advert that someone has paid for via self serve for their subreddit.

Maybe I'm missing something but surely even just throwing up a simple adsense block in the advertising space would generate enough revenue to be worth whatever supposed good will these cutesy cat picture adverts exist to score. Adsense certainly wouldn't "destroy" the trust people have placed in the site... As someone that puts time into reddit I'd be more annoyed if they let the site become so unprofitable they have to shut it down vs. have a few adverts that I can opt out of with a tiny monthly fee.

Would anyone here (that uses reddit) leave if they had proper advertising (that could be opted out of with reddit gold and was not audio / video advertisements, just "standard" web adverts)? I've never met someone willing to leave a website over adverts, if the adverts are reasonable.

Also during the time I wrote this comment I was constantly refreshing reddit.com, so far I have not seen a single non-reddit related advert and I'm at 30 page loads.

(maybe raldi or jedberg or whoever that left reddit and lurks here can explain why this isn't being done, because it's confusing, is there an internal belief that reddit users are so touchy that they'll leave if reddit tries proper advertising?)

edit: oh and for the perfect example, imgur has advertising, what about 75% of popular reddit content uses, and I don't see people boycotting imgur? (of the 100 links in r/all right now 75 are to imgur, 25 of those are to imgur.com which has advertising, so that means 25% of the front page links go straight to imgur with adverts)

edit edit: in an attempt to explain my opinion succinctly, I think the real problem reddit has is the toxic idea that any attempt to make money will alienate the community, when in reality the majority of reddit users don't care and the vocal minority would not leave the site as long as the advertisements were reasonable. People want a stable website that they can be a part of, advertisements don't destroy that. Look at how many people love imgur, 9gag and funnyjunk. Having so little faith in reddit users ability to deal with adverts is to me more "insulting" than the adverts themselves.