Yes, that is one of the real tragedies of the on-line economy. It largely punishes virtue and rewards aggressive behavior, and it is potentially ruinous to resist those carrots and sticks. IIRC there were some posts a while ago about how the content of BB’s posts made it difficult or impossible to use Google’s ads, leading to self-censorship which I got the impression wasn’t enough. And I also got the impression that putting the comments system on a separate domain was in part an effort to make the post page content more friendly to the “good” ad networks. But that’s speculation on my part.
But I do think the behind the scenes rationale and details would be fascinating, if also sad. I think you may underestimate what I find fascinating. (For example, I used to read Groklaw religiously, including the legal filings, even though I am not a lawyer. What is quotidian to you can be fascinating esoterica to others. And, as you note, BoingBoing’s survival to date is rather notable.)