For the Cubs site you mentioned, if you can't sell the "natural"/logical stuff (MLB logo'd items), then you'll have to work harder to sell something else. [Of course, the Cardinals fan in me thinks that a Cub site could do well selling, oh - herbal remedies for depression, for example.
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For the other site - the idea that there is a "recovery" community out there that embraces all of the various and sundry ?A's is a myth. Drunks, druggies, gamblers, et al don't mix well. Hell, you've even got the CA (cocaine) folks who think they're different from a normal, run-of-the-mill junkie.
From a business perspective, I see far more potential in a baseball site than a recovery site.