Considering the multimodal signals of search items is beneficial for retrieval effectiveness. Especially in web table retrieval (WTR) experiments, accounting for multimodal properties of tables boosts effectiveness. However, it still remains an open question how the single modalities affect user experience in particular. Previous work analyzed WTR performance in ad-hoc retrieval benchmarks, which neglects interactive search behavior and limits the conclusion about the implications for real-world user environments. To this end, this work presents an in-depth evaluation of simulated interactive WTR search sessions as a more cost-efficient and reproducible alternative to real user studies. As a first of its kind, we introduce interactive query reformulation strategies based on Doc2Query, incorporating cognitive states of simulated user knowledge. Our evaluations include two perspectives on user effectiveness by considering different cost paradigms, namely query-wise and time-oriented measures of effort. Our multi-perspective evaluation scheme reveals new insights about query strategies, the impact of modalities, and different user types in simulated WTR search sessions.