The original concessions Matz made to Perl have mostly fallen out of fashion now but the core ideas of Ruby, both its deep object orientation and ubiquitous use of blocks, have a simple elegance that have stood the test of time.
Right, but Ruby has its own baggage of design problems, like the lack of namespaces, which are a core idea in Python. I don't argue that one is better than the other, I just see a lot of similarities.
Sure. Ruby has its warts too. Conceptually I find it cleaner than Python overall but I don't think it's possible to design a useful language without making some mistakes along the way. There seems to be two kinds of programming languages: the beautiful ones nobody uses and the messy ones people use to get things done.
In the 9 years I've been using Ruby, I've not once missed having namespaces. A lack of namespaces is a valid complaint against C and Objective-C, not against Ruby—since you can use either nested modules or classes to achieve a similar effect, and often with better design results.