Does it increase the chances that they would sue? Yes, it does. Does it increase the chances that they'd win? Perhaps not, if your arguments hold. Does that matter? No, because you're still talking about stealth distribution of a program that tracks and republishes user data without their knowledge or permission! (And no, a notice buried in the TOU doesn't count.)

Edit to reply to below: Ah, ok. Your phrasing of "piggyback your plugin into popular installers to get this on millions of computers" sounded like you were planning to sneak it in without users' awareness. If it's an explicit opt in, then I would have no great problem with that from a user perspective. (Of course as a user I'd prefer to just install what I want, rather than being presented with options for a bunch of unrelated stuff, but advertising and affiliate programs keep things going, so I deal with it.)

Personally don't have a problem with the part about scraping something I might post on a classifieds site. Whenever I post something on a public web site I expect it to be scraped and to appear on search engines and such. It was specifically the idea of a service running on my computer, watching and potentially publishing aspects of my web use (and who knows what else), without my knowledge or permission that I took issue with.