I mentioned the Hawaiian cards as a possibility for island hopping, but there is no direct flights on Hawaiian airlines from Cincinnati to Hawaii. I would need to get to Chicago. I am only seeing a 30k offer for the United Mileage explorer card. I'm not sure yet if I'll go for AA or United, they book look pretty cheap. I might end up doing a one way from each if I don't get enough miles. Both would be about 40,000 round trip.
I am thinking about getting 2 Fairmont cards to get 4 nights at the Kea Lani in Maui, and then rack up some Hilton points for 2 nights at the Grand Wailea. Grand Wailea is 80,000/night, so if we each got the 2 Hilton cards we'd be covered there.