The task at hand and libraries available also affects how "hard"/"easy" a language can seem. There are many tasks where higher level languages have more facilit

The task at hand and libraries available also affects how "hard"/"easy" a language can seem. There are many tasks where higher level languages have more facilities available to help you. Building a web app will be easier in Python than C, for example. On the flip side, good luck writing a device driver in Ruby. On top of the task-driven reasons, I think the other big reason people find languages easier/harder than others is really a sort of emotional connection. The number of Ruby docs that use the word "joy" or something close speaks to this. Similarly, the people who have emotional responses both for and against Python's syntax and white space might speak to it.