get the Spider Murphy flash book its gorgeous, all the sailor jerry you can. The Revisted book and sketchbooks help Chad Koplenger etc...

Check out Jeff Zuck and pretty much anyone at Name Brand. Anonymous Tattoo, Chris Conn, Tony Hundhal, Bert Krak, Mario Desa, Chad Soner, Todd Noble (of course), Chad Kopelenger, Steve Bolts (NY), Juan Puente

Needles I like a loose 5 or 7 for outlines, but you can go bigger etc - there is not really anythng different, any machine can do what you need if its set up right. Its not really a set up thing, more of a how you use it, thing. Unless you can get your hands on a Jeff Zuck machine, I have one that peppers and whips like butter (heavy fucker)

I am NO expert by any means, but the best thing you can do - try stuff. It's amazing how much taking one of the 30 dollar Sailor Jerry acetate books and just do some paintings.