Python is very popular because it can be used for a wider audience of developers, data scientists, machine learning experts and so on. Like other programming languages, there are beginner to advanced levels of writing Python code. However, like all software, code constantly needs to be maintained as bugs and the need for new features emerge. Although the Zen of Python states that "Simple is better than complex," we hypothesize that more elegant and proficient code might be harder for the developer to maintain. To study this relationship between the understanding of code maintainability and code proficiency, we present an exploratory study into the complexity of Python code on three Python libraries. Specifically, we investigate the risk level of proficient code inside a file. As a starting point, we mined and collected the proficiency of code from three PyPI libraries totaling 3,003 files. We identified several instances of high proficient code that was also high risk, with examples being simple list comprehensions, 'enumerate' calls, generator expressions, simple dictionary comprehensions, and the 'super' function. Our early examples revealed that most code-proficient development presented a low maintainability risk, yet there are some cases where proficient code is also risky to maintenance. We envision that the study should help developers identify scenarios where and when using proficient code might be detrimental to future code maintenance activities.