I find myself doing this a lot with libraries whose documentation encourages an understanding based on intuition, rather than one based on formal concepts. When doing more 'pure' stuff with mostly the standard library, not so much.
Most imperative languages let their users get kind of loose with data design, but I don't feel like Python is especially bad in this regard. Mostly I feel like it depends on how well the programmer understands the software they're working with. And that sense, Python tries to help by encouraging readability. In a sense, you could see almost all computer programming as "poke and hope", though. The variation lies in the size of the poke and the uncertainty of the hope. -- http://mail.python.org/mailman/listinfo/python-list