MrHen comments on The Craigslist Revolution: a real-world application of torture vs. dust specks OR How I learned to stop worrying and create one billion dollars out of nothing - Less Wrong
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I agree that your questions sound important, but there is a bit of a Catch 22 here and not all of them have answers. To get the answers, we need Jim's attention, but we can't get Jim's attention until he sees that we are serious about this. To that end, putting our manifesto on a web site is a very good idea.
As far as closing the ad, my intended design is that closing it would store a cookie that indicates to not show you any advertising on Craigslist. Beyond cookies, it could also be associated with your Craigslist account, though most users interface with Craigslist without signing up for accounts. It can only lower expected revenue, but the kind of people who want to close the ad are probably the kind of people who were not very likely to click the ad in the first place.
Edit: And yes, the title is absurdly long. I have a tendency to abuse title fields in social web apps when there is no effective limit.
So, I guess the first step is finding out how many people we need to get Jim's attention.
50K is a good guess but anything we can do to get a more accurate answer will help.
Your answer for closing the ad works. Is there anyway to find out more details about much that hurts the dollar value? I imagine that someone, somewhere runs ads like that.
You should be able to set an easy lower bound on this. You said, "With 20 billion pageviews a month, a Google Adwords banner would bring in about 200 million dollars a year." Just find actual quotes and keep track of the information. Shop around a bit.
Or find a volunteer around here willing to do it.