Hi @Learntworeed

Sorry for the late reply here. 

This is an interesting workaround that you've been using, but there's not many other ideas that I can think of for this. 

You can simply set your items up without the "Pickup" option enabled, and include notes in the items that indicate the merchandise will be delivered at the actual lesson. That might work a bit better and alleviate confusion. 

You will, however, need to accept each order. 

Maybe try checking out our Square Appointments features as they might work a bit better for you.