Pretty much spent 3 hours on this so far and couldn't find a solution...After searching online for some answers I found nothing that helped specifically. I found the answer and hope this helps some people from going crazy. For me it was simply a horrible UX problem. Under the Shipping option in the Wordpress Admin I scrolled down to where it says Shipping Modules and by chance hovered over the right side of the option FLAT RATE and an EDIT button showed up. I clicked on it and it gave me the option to then update what rates I would use for my flat rates. This is the same thing for Weight Rate and Table Rate. After I configured the settings I went back to the "Checkout" page and tried to purchase one of my products to figure that the option was now configuring what it needed to to process the order, bringing up the Customer details needed to complete the purchase. So glad I found that Edit button but WTH really a grey button on grey background.
Here is the image of what saved the day.
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