Why doesn't and didn't craigslist check for the almost identical emails if they are going through their servers? They could likely dig them out if they keep archives by searching on airbnb, nicest, largest, page, views. Airbnb have the funds now to cough up.
Probably for safe-harbor laws. As soon as they start inspecting things for content instead of server abuse, they are then way more involved and become liable for a lot more shit. They already got a lot of heat from their adult services section, they don't need any more. It's the same reason banks do not want to know what is in your safe deposit box, even if it's mundane.
I hear you, however this is a competitive issue. It's an offense to craigslist by airbnb on craigslist, not an offence from person A to person B via craiglist. I suppose the first issue to look at is whether harvesting and then spam is against the terms of service. The content of those emails isn't genuine, Jill and Sarah aren't real people, they cannot judge the beauty of the properties they proclaim to have seen. It wouldn't be completely Winklevossing for craiglist to be pissed off.
If they turked each property one-by-one, I think that might be fair game.