For me, the best use of Hilton points is to enable travel that I would not otherwise take. For example, I'm going to Chicago later this year to see a concert, and the trip is cost effective because I don't have to pay for a hotel.

However, I will admit that I like staying in unique and historic hotels, so I don't always select the "cheapest" option. It may not be the best use of points, but sometimes staying at a memorable hotel makes the trip more enjoyable.