"I also think that the way Rails is implemented (and to a lesser degree, the Ruby language) takes a little more experience and learning to understand in a meaningful way."

I think this has a lot to do with the person. Ruby and Python are almost identical technically (relative to other popular languages). I personally found ruby a lot more intuitive, and I used python for a year or two before I tried ruby. I'm sure this is a statement about me, not ruby or python.