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I am about to undertake a visual re-design of the site but recently several companies have contacted me about selling ad space on my site. Up until now, I have just thrown in some AdSense text-ads (wherever they fit on the page). Before I do the re-design I want to take a step back and make sure it is both user and advertiser friendly.
Are there any good guidelines and/or resources to help me structure my site with advertising in mind?
Ads are a slippery slope and can be a lot of work if you do them on your own. Things you'll have to worry about include what to do with excess inventory, how to maintain guarantees when you have too much inventory, how to deliver accurate metrics to customers. The companies you'll be competing against do this for a living and have sales people who you'll be competing against. And, unfortunately, it's just not as simple as slapping an image on a page and sending them a copy of your Google Analytics.....at least, it won't be good enough for long. Clients (especially paying ones) always find a way to need more....
That being said, I tell my designers to do two things with ads:
Good luck. Don't go overboard!
You really don't have to (and shouldn't try to) structure your site around advertising. It should be designed based solely on usability. If you want ads, then just leave some space in the masthead area for leaderboard ads, or on the sides for skyscraper ads. That's about all the consideration you need. But even if you don't leave space explicitly for ads (and can't find ways to make space after the fact), a lot of sites are quite successful with inline ads.