I am in a similar situation to you, with a bit more Hilton time each year. I wasn’t in the initial wave of release applicants, but recently I applied for and received the Aspire. I think I’m coming out ahead between the point bonuses, the airline fee credit (I actually have an easy way to use that this year, at least), the resort credit, and the annual free night. If you aren’t familiar with the way AMEX gives airline credits, do some research. For many people they are a nuisance to use. I clearly thought the Aspire package of benefits was worth it. Alas, since I got the card, all my Hilton stays have been in rural settings where I stayed in a Hampton Inn. No upgrades yet, and my research suggests the folks who say they are not to be expected in North America are correct. Similar to you, I already have an Ascend card converted from a Surpass card. I’ll be getting another free night from that soon, and when the new year rolls around will put spending on it to get the $15,000 free night.