Renée De Voursney talking at the AU Ruby Conf about the trials and tribulations of learning Ruby.
She talks about context and how there are so many disparate moving parts to get to grips with before one can "become" part of the Ruby community. Gaining a basic understanding of all the moving parts that encompass not only the Ruby language itself, but the social norms of RSpec, Git, Gems, Github, RVM, *nix, Macs, TDD and various command line tools, is too much of a hurdle for many people to jump.
The biggest problem with a complete novice trying to get into programming is always some sort of feedback loop that will give them the justification to carry on. I'm a great believer in learning by debugging, but at the same time, giving the novice quick wins is important. Get them up and running quickly from nothing (and I mean nothing - no tools installed on their machine yet) to "hello world" in ten minutes.
It's a difficult task. People have a variety of operating systems from various flavours of Windows through Linux boxes and OSX machines. Providing a generic one-size-fits-all is nigh on impossible. Fragmentation sets in. People blog about their frustration and put up tutorials that work on their uniquely configured environments. They try to find work-arounds to annoyances like not having admin rights on computers to circumventing firewall rules that seem to get in the way of any sort of gem installation. It isn't long before someone who just wanted to take Ruby or Rails for a quick ride is hitting their head against a brick wall. And the brick wall is usually just tooling.....it isn't even the code.