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\begin{document}
\title{MATH 9999 - Worksheet Awesome}

\begin{enumerate}
  \item This is an awesome sample problem.
        \vfill
        \vfill

  \item This is a cool setup!
        \begin{enumerate}
          \item Easy difficulty part.
                \vfill

          \item Medium difficulty part.
                \vfill

          \item Hard difficulty part.
                \vfill

                \newpage

          \item Really had part that is better on the next page.
                \vfill
        \end{enumerate}

  \item This is another awesome sample setup.
        \begin{enumerate}
          \item Wow!
                \vfill

          \item Dope!
                \vfill
        \end{enumerate}
\end{enumerate}
\end{document}