I just classify Hilton Points now as an aspirational stay currency, and only for use outside of the US (I am HH Diamond now). Recently I was looking to book 4 nights at the Tokyo Hilton, which would have tallied 412,000 Points. Didn't seem awful with rooms running via AAA at $450/night. Yet I recognized that during that same week, equal or better quality hotels were available in Tokyo in the $325 range.

Then a friend mentioned check out the Conrad, which I hadn't done since I assumed the number of Points needed would dwarf the Hilton. We'll I was wrong, and the Conrad was a total of 400,000. That became in my mind an aspirational redemption, as the Tokyo Conrad clearly is a superior property vs the Hilton, and the cheapest cash rate that week is $725/night.