I am unsure about your AMEX Hilton-->Surpass question, but since you are back at it, I would head over and apply for the 100k Citi AA offer before it expires with your fiance. 200k for the both of you could go a long way!

I also saw in your initial post that you were toying with the option of getting the Hyatt card while on the Diamond Challenge to get two free suite nights. Unfortunately, they do not do the free suite nights if you get the CC while a Diamond anymore. However, you mentioned three nights, so if you pay for one night (or do cash+points), add a diamond suite upgrade to that night, and contact the hotel about the other two nights/that it's your honeymoon, you will probably be fine to stay in that suite for the remaining two nights. Make sure you contact the hotel directly after you apply a diamond upgrade, GP will, at that point, have nothing to do with the remaining reservation.