It looks like the problem is that you're trying to have different shipping methods combine, but that's not how it works. If a package in the order matches the "Hide This Method" rule then that entire method is hidden. So, from your screenshots, it looks like an order that contains items that match both your "Oversize" package criteria and not, both the "Freight - Cost TBD" and "UPS Ground" methods will be hidden and not show a rate.

Conceptually what you need is a generic 'ground' method that sets a $0 rate for oversized packages and pulls rates from your wrapped "UPS - Domestic" method for every other package. The rates for all packages in your order are summed to create a single shipping method rate shown to the customer.

The Category name is the field that is checked. Since a product can belong to any number of categories you should always use a 'contains' check on the name. If there is a possibility of multiple matches you should add a carrot to the beginning and dollar sign at the end of the string (e.g. "^My Category Name$") to ensure a match on the entire Category name and not just a partial match.