Prepayment towards 2020 reservation to trigger credit
I currently have a points stay booked at the Grand Wailea in May of 2020. I have seen where others have contacted international resorts (Conrad Maldives, etc.) and made a payment in advance towards their account to trigger the $250 credit. Does this still work and has anyone had success doing it at a US resort? I just got the card and my first closing date is 7/8 (when the annual fee posts and hence my anniversary date).
I am wondering if I called up the Grand Wailea and attempted to make a $1,000 payment towards my account if it would trigger the $250 credit plus the $200 off $1000 Amex offer for Hilton Hotels in Hawaii along with the $100 off $500 for Conrad and Waldorf Astoria. Any thoughts on whether or not this would work? Would be great because then I could use my $250 again next year when I stay and I'm betting there will be another Amex offer (there has been 2 years in a row).