> Its syntax strongly favors cuteness over familiarity.
Funny, I recently made a stack switch from Ruby to Python, and I had the exact opposite impression. Ruby coding style/syntax tends to favor convention over configuration (at least in terms of Rails setup), while Python to me seems less so.
Ruby also seems to me a bit more consistent across it's versions. One of the biggest gripes I've had about Python so far is how many things are broken across various versions of the language, and the odd way some issues have been handled (having two distinctly different types of strings with distinctly different syntax according to encoding for instance). Perhaps Ruby simply doesn't offer familiarity to you individually.
I'm more comfortable with Ruby as I used it much longer, so I may be biased, and I am not shitting on Python either. It has things I don't particularly dig, but that may be my own bias. Both languages have their pros and cons, and both are certainly viable as scripting languages in this particular epoch of programming.