Unsupervised learning methods -- topic modeling, partition-based and density-based clustering -- produce data groupings without human guidance, yet choosing and evaluating those groupings should not itself be unsupervised. We present \emph{SmartIterator}~(SI), a visual analytics approach that treats the full sequence of grouping results across a parameter sweep as a first-class analytical object. For each method family, SI provides a structured six-phase workflow that guides the analyst through systematic exploration of grouping results -- from quality-metric overview through transition-stability assessment, membership-confidence evaluation, content and context inspection, and recurrent-archetype verification to an informed decision -- building cumulative understanding of data structure along the way. The workflows are operationalized through \emph{IteraScope}~(IS), a coordinated visual display combining quality-metric charts with semantic color encoding, a 1D group embedding with Sankey-style transition flows and violin plots of membership confidence, a 2D group embedding with HDBSCAN-detected recurrent archetypes that highlights iterations capturing all persistent patterns, and domain-specific linked views for contextualized interpretation. We demonstrate the three workflows on: (1)~simulated social-media messages from the VAST Challenge 2011 (density-based clustering, validated against ground truth), (2)~EU population statistics across ${\sim}1\,500$ NUTS-3 regions (partition-based clustering), and (3)~30 years of IEEE VIS papers (NMF topic modeling). The workflows constitute the main contribution: they provide actionable, method-specific guidance for navigating parameter spaces, studying how data structure evolves across configurations, and grounding analytical understanding in domain context -- yielding knowledge about the data that no single ``best'' result can provide.