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It's a matter of personal preference and/or which one you've learnt to live with first.

I like how Ruby's imports work - just load a file, similar to C. On the other hand, modules in Python always felt like something to overcome rather than "just works as you expect".

To each their own, I guess. After working with python/lua, I really appreciate not needing to do manual imports all over. I'm glad ruby makes this so easy :)

Oh, and not needing __init__.py files in order to import something. Goodness, what an absolute pain.

I really like the Python/Lua module system. To each their own...

I agree, but Ruby folks seem to consider C style transitive inclusion to be a feature. I found it and several other aspects of Ruby to be maddening (and productivity-sapping) for the 1.5 years I spent with an otherwise pretty nice language.