... what I'm seeing in Ruby is that the many ways have been transformed into idioms and guidelines. There are no hard rules, but the community have evolutionary evolved idioms that work and found out many of the ways that doesn't work.
Ruby has almost all of the flexibility of Perl to do things in different ways. But at the end of the day, none of the Perl problems tend to show up. Why is this?
Why? Probably because you're not a very good Perl programmer.
A better question is "Why do programmers experienced with a language so often fail to have the maintainability problems that plague novices?" That might have led nicely into a discussion of idioms and the evolution of good style in a language which encourages such things.
See also the discussion why Java fans luuurve their IDEs and can't understand why those of us who can go through the TDD cycle once or twice before Eclipse finishes loading the whole project think that Java's syntax might be a touch verbose. Another fun discussion is "Why don't you Lunix types make one-click installers you can just download and click to install?"
I suppose only the familiar is awesome, and the unfamiliar is stupid and scary.