(1) In your situation, I would definitely have a United card for the free checked bags, and for slightly early boarding when solo. You can pick your poison of which card as long as it has free bags, the Quest should be fine. (2) Since you like Hilton Hawaiian Village, I would seriously consider an Aspire or Surpass Hilton card. Hilton points aren’t high value but you can rake in masses of them from Hilton stays between the card earning bonus, the status, and the occasional Hilton bonus offer. Enhanced chance of early or late check in can also be useful. (3) You don’t seem enchanted with United points, but unless you want to focus strictly on earning Hilton points, or go to Team Cash Back, I don’t see a better choice in your situation. (4) Your AMEX Gold would seem an excellent choice for groceries and the occasional restaurant, but I don’t see a really good way for you to spend the MR it earns. Maybe it should go in favor of a Hilton Surpass for groceries.