I did not start that way as I had a friend that was an accomplished reloader that hit some hard times and sold me his whole set up. However, I think the Lee Kit is a good way to painlessly get started. Then as your knowledge and skills grow, you can upgrade and add on.
Before committing, you might want to go to Ebay and buy an outdated reloading book (or two) and read up on things. The basics of reloading doesn't change that much.