The db structure is very specific for PowerStore and altering how the tables relate via the SKU and product id would be a huge and difficult undertaking. This would require you to essentially rewrite not only the db structure but how all of the queries, inserts, updates, and recordsets for both the front end and the administrative back end work.
If you have the shipped column in your table you would then open up the orders_update page and add in your checkbox to the existing update form. Once this checkbox is in place you can set it's default value by selecting the checkbox and going into the property inspector and selecting the dynamic option. In here you can choose to have the box checked based on the newly added column from your table.
This will give you a checkbox that defaults to the value that is in the column for that order. Next you will edit the DataAssist Update server behavior that is on this page by double clicking it in the server behaviors tab. When the interface opens you can move to the steps where the table's columns have their values assigned. Select your newly added column and for the value use the lightning bolt icon to select your new checkbox.
This should allow you to update the new column in your table on the update page by checking or unchecking the box then updating the record.