> (i.e. someone on twitter will take offense to anything, and they feel they have a legitimate right to never feel offended)
Your post was stronger without this straw man. Do you think a real person would say that they have a legitimate right to never feel offended? I don't think so.
That part of it is easy to mitigate by the auction process. I.e., the mean efficacy of ad placement is reflected in the price of the winning bid due to the usual market forces.
The less quantifiable part of it, "my brand must never appear alongside X," cannot be dealt with in the auction because the recall has to be perfect and it's not feasible to guess how the advertiser would decide all the tricky cases.
While you might be able to automate the process somewhat with ads that aim for direct conversions, it's still extremely difficult to automatically measure the effectiveness of brand advertising.
Advertisers will respond to the masses, not the most outraged hecklers.
Twitter seems to be proving that wrong these days.
When the same social circles are both in PR/HR and the offended class they will consider the same things valid criticism and may go as far as flying in the face of 90% of the quiet consumers of the product's interests.
I dunno. I find Nazis, cat torture videos and pro-ISIS propaganda offensive. But you are right, clearly free speech must be protected at all costs and even made profitable, and clearly it being remove from YouTube and no longer subsidized by major brands advertising would be a huge set back for it.
Maybe people could go to NaziCatTorturers.com and pay to see it or something.
If advertisers have no control over which content their ads appear near then they can legitimately claim, when criticised, that they are unable to pick and choose.
By giving advertisers control, when criticised, the critics can use that same control in order to pressure advertisers to limit ads to inoffensive content only (which, frankly, is almost nothing anymore).
But with the direction "being offended" has taken (i.e. someone on twitter will take offense to anything, and they feel they have a legitimate right to never feel offended) it won't be long before most content is inaccessible.