Nope. It takes at least a couple months of doing daily pentests to become proficient at finding vulns. As to why it can't be automated, it takes a book to answe

Nope. It takes at least a couple months of doing daily pentests to become proficient at finding vulns. As to why it can't be automated, it takes a book to answer that. I'd recommend The Web Application Hacker's Handbook, along with The Tangled Web. There are things you can do, of course. But unless your app is basically read-only, there are almost always one or two noteworthy vulns.