Maybe you do not need a complicated tabular environment for this.
Edit: As requested in the aklingensmith's comment, the title and font background could be set easily with \fcolorbox and color or xcolor packages. Other good option is the mdframed package because their versatility (Note that with this package is not needed call to color packages directly), but also is possible do a fancy box without it.

\documentclass{article}
\usepackage[framemethod=TikZ]{mdframed}
\usepackage{fancybox}
\mdfdefinestyle{MyFrame}{%
linecolor=black!50,
outerlinewidth=0.1em,
skipabove=.5\baselineskip,
skipbelow=.5\baselineskip,
roundcorner=1em,
leftmargin=.045\textwidth,
rightmargin=.1\textwidth,
innertopmargin=1ex,
innerbottommargin=.5\baselineskip,
innerrightmargin=1em,
innerleftmargin=1em,
backgroundcolor=yellow!05!white,
frametitlerule=true,
frametitlerulecolor=black!40!yellow!90,
frametitlebackgroundcolor=black!85,
frametitlerulewidth=0.2em}
\usepackage{multicol}
\begin{document}
\fbox{
\begin{minipage}{0.8\textwidth}
Testing Modifications (highlight or circle) \hrule
\begin{enumerate}
\setlength{\itemsep}{0pt}
\setlength{\parskip}{0pt}
\begin{multicols}{2}
\item Time Limit Waved
\item Exam/Sep Location
\item Questions Read Aloud
\item Answers Any Way
\item Calc/Abacus Permitted
\item On-Task Focusing Prompts
\item Waive Spelling Reqs
\item Revise Test Format
\item Revise Test Directions
\item Breaks
\end{multicols}
\item Other: \dotfill
\end{enumerate}
\smallskip
\end{minipage}
}
\smallskip
{\color{blue} \Ovalbox{
\begin{minipage}{0.8\textwidth}
\centering\fcolorbox{blue!90}{blue!40!black!50}{\color{white}\bfseries ~~ Testing Modifications (highlight or circle) ~~ } \color{red!40!black}
\begin{enumerate}
\setlength{\itemsep}{0pt}
\setlength{\parskip}{0pt}
\begin{multicols}{2}
\item Time Limit Waved
\item Exam/Sep Location
\item Questions Read Aloud
\item Answers Any Way
\item Calc/Abacus Permitted
\item On-Task Focusing Prompts
\item Waive Spelling Reqs
\item Revise Test Format
\item Revise Test Directions
\item Breaks
\end{multicols}
\item Other: \dotfill
\end{enumerate}
\smallskip
\end{minipage}
}
}
\mdfsetup{frametitlealignment=\center}
\begin{mdframed}[style=MyFrame, frametitle={\color{white}Testing Modifications (highlight or circle)}]
\begin{enumerate}
\setlength{\itemsep}{0pt}
\setlength{\parskip}{0pt}
\begin{multicols}{2}
\item Time Limit Waved
\item Exam/Sep Location
\item Questions Read Aloud
\item Answers Any Way
\item Calc/Abacus Permitted
\item On-Task Focusing Prompts
\item Waive Spelling Reqs
\item Revise Test Format
\item Revise Test Directions
\item Breaks
\end{multicols}
\item Other: \dotfill
\end{enumerate}
\smallskip
\end{mdframed}
\end{document}