Synthetic data is increasingly critical for contact centers, where privacy constraints and data scarcity limit the availability of real conversations. However, generating synthetic dialogues that are realistic and useful for downstream applications remains challenging. In this work, we benchmark multiple generation strategies guided by structured supervision on call attributes (Intent Summaries, Topic Flows, and Quality Assurance (QA) Forms) across multiple languages. To test downstream utility, we evaluate synthetic transcripts on an automated quality assurance (AutoQA) task, finding that prompts optimized on real transcripts consistently outperform those optimized on synthetic transcripts. These results suggest that current synthetic transcripts fall short in capturing the full realism of real agent-customer interactions. To highlight these downstream gaps, we introduce a diagnostic evaluation framework comprising 17 metrics across four dimensions: (1) Emotional and Sentiment Arcs, (2) Linguistic Complexity, (3) Interaction Style, and (4) Conversational Properties. Our analysis shows that even with structured supervision, current generation strategies exhibit measurable deficiencies in sentiment fidelity, disfluency modeling, behavioral variation, and conversational realism. Together, these results highlight the importance of diagnostic, metric-driven evaluation for synthetic conversation generation intended for downstream applications.