For tech-savvy people who understand the issues an ad-blocker might be worthwhile even if it means some websites don't work temporarily while the ad-block developers think of new ways around things. For more typical web users though, the Washington Post's approach will result in a line of thought like "I installed that software and my Internet broke because some websites didn't work any more. I'm going to uninstall it." It's not unreasonable to believe ad-blocking might never become a mainstream technology that enough people use for it to change the way websites are funded. That, I would argue, would mean the ad industry has won the war.
The only ads I do block are the 'recommended for you' fake content from outbrain, zergnet, gravity and taboola. Just terrible.
I understand that position. But that's a losing position. It's an arms race, ad-blockers will always find clever ways to bypass these schemes then consultants will come with more complicated scripts that will make web pages heavier and harder to visit for those who don't block ads ...
The Washington Post certainly is not going to win that war. The only solution for them on the long run is all their website behind a paywall, like the Financial Times.
I'm curious if youtube is going to do the same, since they introduced an ad free paid offer.