I’m interested in this as well. Hilton’s policy is that you can make a booking up to one year in advance, so if you were looking to book five nights on points (to get the 5th night free) you’d have to wait until the day the 5th night is available to be booked in order to have all the nights on one reservation. For an in demand hotel the rooms may be booked if you wait too long. Would it be possible to instead make 4 individual bookings each day as rooms become available and then call on the 5th day and ask them to consolidate the 4 individual bookings and add a 5th night for free?