Nice article! One very important thing I miss in your article, however, is a comparison of documentation. Good language and library documentation is as much a part of a language as its most common interpreter or its standard library itself, which you do address. Finding your way in a language may actually depend a lot more on the actual docs available than on any "principle of least surprise" or whatever. Only after using both Python and Ruby for various projects, I realised how important this is - coming partly from a PHP background. No matter how ugly PHP as a language might be, its documentation, both in terms of quality of content as ease of use/accessibility, is way ahead of both Ruby's and Python's.
I personally find the python documentation extensive, but very very messy. A list of dict methods is here, things about how lists work is there, and please look underneath the table for string methods, thank you. Oh and if you look in a totally different place, you'll find that there are also global functions operating on strings, with the same names. Naturally, we did not make a link between these two places. To my experience, Ruby performs better here, having a very decent, but maybe a bit concise, reference for built-in classes and modules that is up to date. Its standard library is, i believe, documented even worse than Python's, though (but at least a bit more functionality is considered built-in).