To add to my original post, I also did a dummy search on another random midwestern city for November dates, and found multiple Hilton properties there offering award redemption options. I could keep testing cities of various sizes all day, so I guess what I'd appreciate from someone here is your opinion on whether HHonors is typically a difficult program to redeem with, or if I'm missing something to make this easier on myself.
I've become frustrated early on, only because with SPG and PC I can easily find award options for similar searches ~6 months out, in the same popular big cities.