Software engineering and development is well-known to suffer from unplanned overtime, which causes stress and illness in engineers and can lead to poor quality software with higher defects. Recently, we introduced a multi-objective decision support approach to help balance project risks and duration against overtime, so that software engineers can better plan overtime. This approach was empirically evaluated on six real world software projects and compared against state-of-the-art evolutionary approaches and currently used overtime strategies. The results showed that our proposal comfortably outperformed all the benchmarks considered. This paper extends our previous work by investigating adaptive multi-objective approaches to meta-heuristic operator selection, thereby extending and (as the results show) improving algorithmic performance. We also extended our empirical study to include two new real world software projects, thereby enhancing the scientific evidence for the technical performance claims made in the paper. Our new results, over all eight projects studied, showed that our adaptive algorithm outperforms the considered state of the art multi-objective approaches in 93 percent of the experiments (with large effect size). The results also confirm that our approach significantly outperforms current overtime planning practices in 100 percent of the experiments (with large effect size).