I don't mean to offend, but you might be over thinking this a bit. Either you stay at Hilton's enough that the benefits of the card are worth it or they are not, but there is no way in the world that Clear provides enough value to be the decider in IMHO.
I'm not offended at all, since I knew very little about it I appreciate the edification.
We stay at Hiltons a lot but don't like having to be pigeonholed into timeframes. With the possibity of only one resort stay a year, I guess we'll have to plan it for, say, June 28 to July 3 and split the payment.
Likewise being pigeonholed into when we can use the airline credit. For example, this year had a bunch of money still to spend so upgraded all our seats to PC on Alaska, they ranged across several months. Won't be able to do that next year.