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Maybe I am a bit late in my response, but even still, you couldn't possibly have advanced too far with Python in this time range.
Your reasoning for using Python over Ruby is so redundant I can hardly bare it. Ruby is a far nicer looking, cleaner syntax, and probably altogether easier to use language than Python. Python's only advantage is the fact that it is older, and thus being older it has been exposed to more and supports more. Python also spread earlier than Ruby, if you ask me, it seems like Ruby just started to spread in recent times. Never choose one language over the other because you are more familiar with the tools! This is the reason why many people I know are afraid to get away from Visual Basic 6. They know the software (keyword here, too bad the keyword isn't 'language'?) too well to leave it alone.
Give Ruby a chance the same way you gave Python a chance.
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