Learning to DJ?

cloudkj asks: "Being a geek and a music fan, I've played with various applications for creating and mixing music. DJing has always been an interest of mine, but I've never had the time nor the resources to take it up as a hobby. Now that I've left college and started working, I have the time and the funds to allow me to explore DJing. What are the best ways to start learning how to DJ? Are there any spectacular pieces of digital DJ software out there that a aspiring DJ needs to have? How does a DJ transition from digital to the real thing?"