Answering my own question:
The problem seems to be specifically with using formatting commands such as \bfseries in the before/above part of the command. Somehow they end up influencing how the filler part works. One solution I found was using \normalfont first thing in the filler part and reapplying any formatting to the page number afterwards (if desired). Example:
\documentclass{book} \usepackage{titletoc} \contentsmargin{2.55em} \titlecontents{chapter}[0pt]{\scshape}{\thecontentslabel}{}{\normalfont\hfill \contentspage[\bfseries \thecontentspage]} \titlecontents{section}[2cm]{\bfseries}{\thecontentslabel}{}{\normalfont\hfill \contentspage[\bfseries \thecontentspage]} \begin{document} \tableofcontents{} \chapter{Lorem} \section{Ipsum} \end{document}
This now results in
However it should be noted that \contentsmargin seems to also play some part here, since I needed to add it to the first example in order to get at least strongly noticeable misalignment. I very much welcome thoughts and explainations from the experts why that is.