Preference learning is a widely adopted post-training technique that aligns large language models (LLMs) to human preferences and improves specific downstream task capabilities. In this work we systematically investigate how specific attributes of preference datasets affect the alignment and downstream performance of LLMs in instruction-following tasks. We use a novel synthetic data generation pipeline to generate 48,000 unique instruction-following prompts with combinations of 23 verifiable constraints that enable fine-grained and automated quality assessments of model responses. With our synthetic prompts, we use two preference dataset curation methods - rejection sampling (RS) and Monte Carlo Tree Search (MCTS) - to obtain pairs of (chosen, rejected) responses. Then, we perform experiments investigating the effects of (1) the presence of shared prefixes between the chosen and rejected responses, (2) the contrast and quality of the chosen, rejected responses and (3) the complexity of the training prompts. Our experiments reveal that shared prefixes in preference pairs, as generated by MCTS, provide marginal but consistent improvements and greater stability across challenging training configurations. High-contrast preference pairs generally outperform low-contrast pairs; however, combining both often yields the best performance by balancing diversity and learning efficiency. Additionally, training on prompts of moderate difficulty leads to better generalization across tasks, even for more complex evaluation scenarios, compared to overly challenging prompts. Our findings provide actionable insights into optimizing preference data curation for instruction-following tasks, offering a scalable and effective framework for enhancing LLM training and alignment.