Hi all,

I'm hoping to go to Kauai with the wife for our 5-year. I'll be using United miles (from my Ultimate Rewards account) to fly us there in January, and am considering getting the Chase Hyatt card for the free 2 nights at the Hyatt Kauai. I'd be there about 7 days, and could see shelling out points for another 1-3 nights on top of the 2 free nights (for a total of 4-5 nights at the Hyatt).

I'm thinking about doing the Diamond Challenge so as to make our stay even better, and have 2 questions:

1) How should I time everything? As far as I see, I could (a) get the Hilton Reserve card NOW, then get matched to diamond with the challenge at Hyatt (by virtue of Gold HHilton from the reserve card), THEN get the Hyatt card (such that my 2 free nights would be suites). OR, I could (b) Get the Hilton reserve card and Hyatt card WHENEVER, book at Hyatt now, and just make sure to do the Diamond challenge BEFORE I LEAVE, so that I'm actually a diamond *during our stay*.

I think B makes more sense, except that I'd want to book as far in advance as possible (to make sure there are no problems), so I'd definitely be BOOKING as a platinum (b/c of the Hyatt card), and NOT as a Diamond. Is that a problem?

2) Is the above worth it for a few days of Diamond versus platinum at Hotel Kauai? The much simpler option is just to get the Hyatt card and use 2 free nights plus some points for a stay as platinum (by virtue of the Hyatt card). Can someone *with experience at the Hyatt Kauai* give their opinion as to what one gets for the extra hassle and credit inquiry of getting the Hilton Reserve and status matching?

Thanks!!