I wonder why CL doesn't create an API and charge for it's usage. The data is clearly valuable and they own it, but that doesn't mean that it can't use multiple views.
This is only useful if the teams scraping CL have budget to pay a market rate for the data. Considering that CL seems to have a lock on this data for many markets, I'm guessing that's worth a lot of money (which startups will not be able to afford).
If they cannot afford, then they should not be there. Scraping illegally is not a long term solution. Craigslist should conduct some market research from their end to charge a "reasonable" fee which fills in their coffers as well as allow development an ecosystem around their data. Even DuckDuckGo pays for Yahoo! BOSS Search API to show their results. Not sure why CL hasn't thought about it.
I see a lot of great (spectacular in some cases) videos being posted on vimeo. Most of these are as you said, young people with 5Ds making short films. However, it is still a leap of imagination to think that people will switch to shorter content over films and TV.