As far as anonymity, well, first off if you start with calling them a squatter, I will add a 0 to the price I will sell to you if I respond at all.
Second, 20$ is a profit if you don't value time. Some of the big guys have 100k names and get tons of offers every day. Is 20$ worth the time to negotiate, escrow and transfer for someone making 20 mil a year? nope.
As far as contacting, most anonymous whois emails end up in a real mailbox I believe. There are other ways to track them down, for example getting a broker. Holding large portfolios, even if they aren't converting on traffic, can convert on a sales model. Average portfolio churn rate is around 2% for the big guys I believe. Parking helps cover costs, but sales generate the $$$.