This subject is similar to "caliber wars". I do not mean to start a urinating contest, but will speak from my own personal experience.
As for equipment, I have the Dillon XL 650.
http://www.dillonprecision.com/#/conten ... d/1/XL_650
I fell for the "start with a single stage press first", which is what sales peeps want you to do, so they can sell you a progressive later. It was a mistake for me to start out like that because it took sooooooooooooooooo long to load even a couple hundred rounds.
You CAN start with a progressive, and take it slow. A progressive press can be used as slow as a single stage, with double checking every step until you get comfortable with it.
Read everything you can get your hands on. I think the Lee and Speer are rated as the best. Lee's "The ABC's or Reloading" is a great place to start.
http://www.reloadbench.com/main.html is a great website, and has a good forum. Spend some time there learning from the wisdom of others.
Then there is the NRMA website
http://www.reload-nrma.com/videos.html that has videos of every step in the process.
It won't take you long to get competent and confident, and really start churning out the rounds. When I go a while without reloading, I go back and reread the manuals before starting up again.
FWIW: When I first started reloading, I would run some rounds through a Ruger pistol before I would try them in the Walther, Kimber or Sig.