How to align cell content correctly?

Question

I would like to have in some table a cell that contains text and graphics wrapped around. The table itself will need several pages. However, tabularx aligns the content of the two columns nicely whereas LTXtable doesn't. If I'm not mistaken, tabularx cannot split the table onto more than one page. I am using TeXLive under Ubuntu (if that matters). I tried several other packages as well but either the content was aligned (no pagebreak possible) or pagebreak was possible (but the content not in one line). Other packages like wrapfig didn't help either.

Is a "compromise" possible?

\documentclass[paper=a4,draft=false,fontsize=14pt,DIV=calc]{scrartcl}
\usepackage[ngerman]{babel}
\usepackage[T1]{fontenc}
\usepackage[utf8]{inputenc}
\usepackage{nag}
\usepackage{ltxtable}

\setlength{\parindent}{0pt}
\input{insbox}
\begin{document}

\LTXtable{\textwidth}{mwe_insbox_table.tex}

\begin{tabularx}{\linewidth}{lX}
    left column & {\InsertBoxR{0}{\begin{minipage}[t]{0.4\linewidth}\centering \rule{5cm}{5cm}\end{minipage}} Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. }
\end{tabularx}

\end{document}

The file mwe_insbox_table.tex contains:

\begin{longtable}{@{}lX@{}}
left column & {\InsertBoxR{0}{\begin{minipage}[t]{0.4\linewidth}\centering \rule{5cm}{5cm}\end{minipage}} Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. }
\end{longtable}

Answer 1

It works with \ltablex if you add the directive \keepXColumns and a negative vertical spacing at the beginning of the X cell. I also simplified your code: no minipage environment to type, with \@minipagetrue on entering the X column:

\documentclass[paper=a4,draft=false,fontsize=14pt,DIV=calc]{scrartcl}
\usepackage[ngerman]{babel}
\usepackage[T1]{fontenc}
\usepackage[utf8]{inputenc}
\usepackage{nag}
\usepackage{ltablex, makecell}
\usepackage[svgnames]{xcolor}
\setlength{\parindent}{0pt}
\input{insbox}
    \makeatletter
    \newcommand*{\compress}{\@minipagetrue}
    \makeatother

\begin{document}

\keepXColumns
\begin{tabularx}{\linewidth}{l>{\compress\arraybackslash}X}
   left column &
   \vspace*{-\baselineskip} \InsertBoxR{0}{{\color{Tomato}\rule{5cm}{5cm}}} Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text. Some silly text.
\end{tabularx}

\end{document}