As for the hotels, the Hyatt card and Chase Sapphire Preferred are a great option. There is an amazing Grand Hyatt on Kauai and a nice Hyatt Regency on Maui. Using 2 Hyatt cards and 1 Sapphire card I am staying 7 nights at the Grand Hyatt (which is over a $3000 value). Each Hyatt card gives you 2 nights free and additional nights are 22,000 points. The Sapphire Card gives you 50,000 points which can be transferred to Hyatt. That leaves me 16,000 points short but by the time I reach my minimum spends, I should be almost there. I will transfer the rest over from an old Chase Freedom I have.