What we've found works is this:
1. Beginners need a curated stack by someone they trust. "Here, this is the stack to learn from; stop wasting time evaluating and get started."
2. Learn about the people, personalities, and community that make the tools. Understand the reasons for their creation; keep up with the conversations.
#1 from above gets beginners unstuck, while #2 will allow them to slowly evaluate different pieces of the stack over time. It's important to understand the "why", not only the "how".
For our courses, we use a mix of the two stacks. For our intro to Rails course, we use: erb, sqlite in dev and postgres in production, fat models and skinny controllers. For our intermediate course, we use haml, rspec, postgres. And finally, for our advanced course, we use "outside in" BDD with Cucumber and introduce the concept of service layers.
We've found this to be a great approach to introducing newbies to the "37 Signal stack" and growing them into the "Prime stack". The goal is to let them figure out their own preferred stack over time, and be productive no matter which stack is in front of them.