Originally Posted by hbcobra

I am a longtime Marriott member and am starting out from scratch with Hilton. What are your recommendations on the cards that I should get (if any), and in what order should I apply for them, to maximize my return? The main goal here is to accumulate as many points and free nights as possible for a big trip in late 2019 or summer 2020. I already have Priority Pass and Global Entry, so those perks won't move the needle for me by themselves, but I am not opposed to getting the Aspire card to obtain its Diamond benefits. Thanks!