Hello, hope you are well and safe. Your project description really caught my attention. I'm extremely interested in your project because of it's related to woocommerce and I would like to work on this. I am very confident to fullfill your requirement asap. I'm an expert in making new plugins for woocommerce, I've great experience more than 8 years in this field.
I don't know which other functionality you added already, and you need to add two checkboxes within there in new two columns(easily possible but entire row is a link type, you can't checked this checkbox!).
Sounds not good appearance! Customer's note always be there to read customer's extra request if any, Private notes like optional. But main thing is why you want to hide or show and for whom?
Or you want a new column there for read customer's note?
Please discuss further and exact main output or functionality. Please chat need more discuss. Thanks