Shipping Settings - Order can't be shipped to address (at checkout)

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I have Shopify Advanced mainly for shipping purposes. I ship to the US and Canada. I use CustomCat, Printful and SPOD for POD products. I have not been able to set this up correctly since I switched to the Advanced and it is costing me more money because customers cannot checkout with certain products.

The issue today is CustomCat products. This app doesn't link to Shopify properly from what I can tell at this point.

How do I set up each of the Shipping profiles correctly? It is really frustrating and I have spent more hours trying to figure out shipping than I have on anything else. I thought paying over $400 for this Advanced membership would have made it easier.