Coming from the shell, one of the most annoying things about Python is working with files. In the shell I can read and write to files on the filesystem with basically no friction and no extra infrastructure. Just a "cat" command or a <, >, or >>. The ease at which input and output can just get tossed around in the shell is the biggest thing I end up missing when I graduate up to any "real" language.

I remember when I first learned how to work with files in Python and thought "Damn, y'all live like this?"