It would be my opinion that PG probably doesn't care.
If this wasn't already clear, we're not looking for the sort of obedient, middle-of-the-road people that big companies tend to hire. We're looking for people who like to beat the system.
I understand that, going against unjust rules, regulations and industry monopolies because otherwise economically; people pay more (taxi monopoly) or inconvenienced (no driverless cars allowed).
But these black hat email marketing tactics are akin to harassing people automatically without discrimination. Posted two properties? At least two emails from two 'women' advertising AirBnB. It's effectively destroying Craigslist if every company including my potential own escape backlash for spamming users.
Some people like me look to PG as a chaotic good role model for entrepreneurs.
I think most people are looking for PG's general opinion over the issue. He has had written about certain "naughtiness" in his essay(s?). To what extent does he think it's OKAY?
If this wasn't already clear, we're not looking for the sort of obedient, middle-of-the-road people that big companies tend to hire. We're looking for people who like to beat the system.
http://ycombinator.com/howtoapply.html