Members are constantly dissing Hilton Honors and Hilton Honors Points. I agree it would be nice if every room could be reserved for the old 40,000 points or less the way it was when I became a member. However, recently I have reserved some nice vacations using my points for reasonable numbers of points.
Washington DC is very expensive, but at 50,000 points a night I made two 5 night reservations for my Daughter, SIL, Grandchildren, wife and I in downtown Washington DC in August for 400,000 points since you get the 5th night free.
At 30,000 points a night I made two 2 night reservations for Daughter, SIL, Grandchildren, wife and I for the summer of 2014 in Oneonta, NY so we could visit the Baseball Hall of fame in Cooperstown.
NY City is very expensive, but at 60,000 points I made a reservation for last July 3rd in midtown Manhattan for 1 night so we could attend a show.
Every September we attend my wife's class reunion in Tarrytown, NY for 30,000 points a night.
Honolulu is very expensive, but we have extended our timeshare stays at the Hilton Hawaiian Village for 50,000 points per night.
The 5000 point gift is small and won't get you a night on its own. But 5000 points here, and 500 points there, and a few thousand points a month for credit card expenditures using the Surpass Card, and paying your substantial maintenance fees with your Surpass Card and you can have some nice vacations for free.