How do you measure wheter what you just typed is more expressive to me than raw ascii numbers representing the characters you typed? ...

Why do you need to make a small problem big, just to sound "academic" ?

..you can easily measure the expressiveness of any given language by how easily you can understand it based on what you already know (i.e. your mothertongue language).

The same old principle of the least surpise..

And flexibility ? How would you tell if one language is more flexible than another ? It takes no academic graduation to understand that flexibilty is the degree of freedom the language allows you in combining the language fundamental "bits" in syntactically correct ways.

So, getting back on topic for you to understand better... :

Ruby different Ways To Loop http://www.ruby-forum.com/topic/151837

The beauty of Ruby through examples http://www.ruby-forum.com/topic/217762

Good reading.