Thank you very much for your responses. I'm definitely open to looking at Hilton, Hyatt, and Starwood properties. Like many people on FT, upgrades on business travel are helpful, but are really important when traveling on leisure with my wife and can be fully enjoyed.
Having said that, I've narrowed my options further:
1. The Hyatt looks amazing, and I found out that Hyatt will provide an interim match of 60 days to Diamond for Marriott Platinums. Hyatt wants another 12 stays within 60 days for you to retain the status, but I think that I can swing that. Also, my wife and I could both sign-up for the Hyatt credit card and essentially get 4 free nights total (2 sign-up nights for each of us) for the total $150 annual fee. Plus, we have enough points for the 5th night.
2. I had been looking at Hilton credit card sign-up bonus options, and had not encountered the HH Surpass - just the Citibank 30K and standard Amex 20K bonuses. That's definitely an intriguing option if it provides 40K miles and HH Gold immediately. Plus the ability to convert AA miles to HH miles. Not sure if Hilton will match my Marriott Platinum status or not. A few years ago I did a challenge to earn gold, but since then stayed away from Hiltons. Also, as another option I noticed on the useaamiles.com website, you can redeem for the Conrad in the Maldives.
Will keep everyone posted on what we decide. Thanks for the input. Would appreciate any additional input you have.