I just finished Enterprise Rails and want to tell you what a capital, outstanding, helpful book it is. I was sad when I finished it!
I've been building a startup site of moderate size, not even something you'd call enterprise yet, for the last 3 years. When I started I was just the sort of naive and overconfident Rails guy this book is aimed at. The author has been through all the scaling issues involved with running a popular website and the book is chock full of useful advice and examples. I wish I had read it way back when I started as I have made many of the mistakes he warns about and had to learn the hard way. Dan shows you how to avoid painting yourself in a corner with overly optimistic/naive design choices up front. He shows you how to design things properly from the start, with a special emphasis on using the native features of a relational database instead of doing things at the application level, and how to keep things organized. I love love LOVED this book.