Suitable conjugated polymers for use in high performance organic photovoltaic devices, field effect transistors and other low-cost devices have been identified during the last decade. Next to the synthesis and investigation of new materials with yet improved performance, the preparation of existing copolymers needs to be improved with respect to reproducibility, purity, costs, atom economy, and environmentally benign and sustainable protocols. In this contribution we shine light on the fundamental limitations of direct arylation polycondensation (DAP), which is a recently emerging transition-metal catalyzed polycondensation technique that can potentially outperform standard methods such as Stille or Suzuki polycondensations. DAP protocols require less synthetic steps, hence are faster and cheaper, and produce less (toxic) waste. In particular, we will address important and mostly unsolved questions of detrimental side reactions of DAP which limit scope and applicability of this intriguing method. Issues of C-H selectivity in monomers with multiple C-H bonds, homocouplings, and chain termination processes are discussed and exemplified by presenting several examples of conjugated polymers with high charge carrier mobility, photovoltaic performance and luminescence.