They're not stupid questions at all.

The purpose of creating 100 sites is to show that the community can create sites faster than the lawyers can shut them down.

If you follow the steps above it's perfectly safe: Tor hides your IP address from the sites you're visiting, so the webmail provider and the hosting provider can't discover your real identity.

If a lawyer sends a cease and desist notice to your site, the hosting provider will take down the site and send an email to the webmail account, but nobody will be able to find out who you really are. It happened to me, and I'm still here. Then you just go back to step 1 and create another site.