I've only recently started with Ruby on Rails myself. Check out my insights, procedures, and deployed projects at http://www.jasonhsu.com/ror.html . I put this page together partly as a resource for the Ruby on Rails community but mostly as a reference for myself.
The things I insist on: 1. I do my Ruby on Rails development in VirtualBox. Like you, I found it tricky to properly set everything up - you need the right versions of multiple packages. It felt like I had to make sure all the planets were properly aligned. VirtualBox allows me to install a Linux distro on a virtual drive and take snapshots. If I screw up, I can return to a previous snapshot rather than have to start over. I know that many people like RVM. I tried to use it, but I couldn't get it to work, so I stick to using VirtualBox snapshot to seamlessly switch from one snapshot to another. (I recommend using one of the newest VirtualBox versions so you get the clone feature.) 2. I insist on deploying early and often. This allows me to spot any deployment problems early on and correct them. I once tried waiting until the end to start deployment (because the book did), and I couldn't get my app deployed.