A multi-selection system allows selection of multiple displayed items in a GUI, and processes an underlying data set based on the selection. Users may utilize swipes or concurrent point interactions with the GUI to co-select items. The system identifies actions to perform for selected items based on selection criteria associated with the selected items, or mapping data that maps the selected items to actions. The system automatically identifies grouping criteria for data returned from performed actions and displays resulting groups for further user selection. The system provides suggestive visual highlights that identify commonly co-selected items in the interface. The system collects instrumentation items, for historical usage data, that record aspects of users' interactions with the system. As such, the system may identify, from the historical usage data, sets of commonly co-selected items, mappings between combinations of items and one or more actions, productive arrangements of items displayed in GUIs, etc.