I’m gonna hit $15,000 in spending on my Ascend in December... I am thinking of pursuing this strategy
1) Apply for Aspire in early September, get 1 free weekend night later this year
2) Have two weekend nights for use in Calendar 2019
3) Use Ascend for dining/grocery spend through 2019, earn 95,000 Hilton points plus a free night for 2020
4) Use Aspire for any Hilton stays. Benefit from various credits (I can probably use the airline credit, but no clue if I will stay in a Hilton resort in any given year).
Basically get two free weekend nights, at least 95,000 points, Diamond status and credits for $545 in fees annually. ,