Thanks so much for all the helpful replies so far!

@Mommypoints: So you were given 1 day worth of free cabana rental, or was that for the duration of your stay? From what I hear, the pool can get crowded and those cabanas come in very handy!

@W2B: Thanks for the tip! I'll look into staying in that wing. Free access to the Anara Spa facilities would certainly be nice!

So, if I AM successful at getting a diamond status match, the best option is to worry about having Diamond status, NOT when I get the Hyatt card, but instead when I BOOK the hotel...OR when I STAY at the hotel? It sounds like the best time to be diamond is when I STAY at the hotel, yes? And doing so means:

- Possible to get an upgrade/talk to the social media team in advance and see what happens

- Free access to Anara Spa

- Free breakfasts in the morning and evening snack (this is actually a big deal for us, I think)

- Free Diamond amenity, like a cabana rental (I'm guessing it's for a single day only).

Am I missing anything?

Any other thoughts/suggestions/strategies?

Thanks again for being so helpful. And sorry to you other folks for not asking the most original question in the world. :P I definitely couldn't find this exact question answered anywhere (though there are a LOT of related topics), so hopefully this thread will help others with similar questions!