Reply from WebAssist
WebAssist sent me the following information and it worked perfectly.
Here are the steps that I took. I first made a page like you have with a form and recordset. I added bindings from the recordset to the form elements. My form included a single checkbox and a text field. I then added the standard repeat region server behavior.
When I got the repeat region in place I previewed the page to ensure that it was working as expected. Once I confirmed this I added in the DataAssist Multiple Insert server behavior. In it I selected the repeat region and for the 'skip if empty' option I choose the checkbox. I selected the table to insert into and on the next page just associated the value I wanted to be inserted into that column. In my case the value was held in a text field, but it could also come from a hidden form element if you want to have a cleaner looking display.
Once I finished this I tested the page out by saving and previewing it. I checked some of the boxes and clicked the submit button. The records that I checked were inserted without issue.