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.
You can actually get 60,000 for the regular hhonors amex. See
this thread. The thread and the application says 62,500 never figured out the last 2,500 I think its for getting a second card tied to the account. Plus this card has no annual fee and gets you silver status just by getting the card.
You can sign up for the hhonors MVP program and get gold status with
4 stays. Although the free gold with the surpass is a great deal and if you spend $40,000 a year you can get diamond with no hotel stays.
The ability to convert AA miles to HHonors points is provided by AA not any card. Its basically 6 miles to 10 points. Up to 150k miles (250k points) a year. But you say your wife has 200k miles as well so you can each convert up to 150k and put them into the same account.
May 31 to June 5th by my calculations thats 5 nights so 195,000 hhonors points (4 night axon award + 1 single night award).
Personally I would say stay at one of the hilton properties. Get one of the hhonors amex cards, then transfer what points you still need from AA. Should be nice and simple.