I am trying to choose between applying for either the Hilton Honors Amex or Chase Sapphire for 50,000. HH Honors will get me: 20,000 points on first purchase, 30,000 points for spending $500 in the first 3 months, 10,000 points for first 4 stays charged to my card plus an additional 2,500 for signing up an additional cardmember. Total of 62,500 but realistically, I wont pay to stay 4 nights, so I will only get 52,500. The great part is it will extend my gold membership ( which expired 2 months ago) for another year ( free breakfast and upgrades) and I could stretch the amount of free stays using their new points and cash system. Currently I have only 22,000 points in my account plus a $200 one night Hilton gift certificate. Chase sapphire will give me 50,000 points which I can use to apply to any hotel. I like to stay in 4-5 star properties so realistically this may only get me 2, maybe 3 nights, but they will be point generating stays which is always good. Currently, I have Starwood gold and Priority Club Platinum status.