I guess what I'm struggling with is, in a repeating section, everything is related to a "row." The way this is set up you would have two identical lists that could be different (meaning different items selected). I'm not groking why two different lists are needed if they are going to have the same options. So, regardless, going on your example here's what I understand: Repeating Section Field 1 List of stuff (field 2) Item 1 Item 2 (selected Item 3 Item 4 (selected) Field 3 Field 4 Field 5 List of stuff (field 6, "summary" of field 2) Item 1 (can't select, because not visible) Item 2 (visible, can unselect) Item 3 (can't select, because not visible) Item 4 (visible, can unselect) Without messing around with it, here's the approach I would start with: Field 2 would be a multi-select menu (not sure Roll20 supports this, I've never tried a multi select field in a character sheet, so if it's not, it would be a series of checkboxes) Field 6 would be a series of checkboxes, regardless of how I configure Field 2. All these fields are hidden by default (using CSS) A sheetworker would watch for changes to Field 2 and when an item item is selected in field 2, it would select the appropriate checkbox in Field 6 (making it visible). If I select that item in 6, it would be hidden again (but field 2 would remain checked). Field 6's visibility would depend on the item being checked/selected. Edit: Re-reading the acceptance criteria again, I'm confused by this line: The method of removing items is not performed from the summary. How are they removed from the summary? From the original field? Regardless, I would still use the above approach with one change, instead of displaying the checkboxes in the summary, I'd use named spans. For example: <span name="attr_field6_2> Or something like that. You'd still need the hidden input fields so the span would be visible if the item was unselected.