The Hilton Aspire is a great card. You definitely get your value back on the $450 AF, and you certainly seem to have plans for its benefits.
Just a few thoughts --
- Are you looking at the Aspire as a keeper card? If so, double dipping (or triple dipping) doesn't really matter. If you plan to hold it for only a year then cancel, then you could triple dip the $250 airline credit if you timed your application for mid-November through most of December.
- Amex has gotten a lot stricter against customers who sign up for a card just for its signup bonus but put little to no spend on it after meeting MSR, then cancel after their year is up. If Amex deems you a "gamer" based on your "history" with their cards, they may deny you bonuses on any future card applications. So whoever applies for the Aspire, make sure to keep the card in their wallet and continue to put spend on it.
- The CSR and Biz Plat already gets you Priority Pass access for the cardholder and 2 guests (at most PP lounges/restaurants).
- The Biz Plat already gets you Gold status at Hilton. Diamond is obviously better.
- Since both you and DH are still under 5/24, are you sure you wouldn't rather get a few more Chase cards first? If you're open to business cards, Chase's three Ink business cards can net you at least 180k UR per player. And you can use UR to book cash rates at Hiltons or any other hotels (but you likely won't earn points on that cash stay).