I was offered a long selection of options at the Hilton Montreal Bonaventure, including prepaying for a room upgrade to the Executive Floor for $40. Here is the offer, presented in my Hhonors Reservations summary as "Order Requests upon Arrival":
Make Your Hilton Hotels Requests Upon Arrival
Thank you for choosing the Hilton Montreal Bonaventure. In order to make your stay more comfortable, listed below are a variety of amenities you can select in advance of check-in and benefit a 15% rebate of the prices listed in the Room Service Directory. Just click on your selection and indicate the quantity, and we will have the amenities waiting for you when you arrive. It's just another way the Hilton Family recognizes your individual needs whenever you stay with us. Pamper yourself and select one of our newly renovated Executive rooms. If you have any questions or comments, do not hesitate to contact our Guest Service Manager.
I called the hotel and was told that as a Diamond I could still expect to receive an upgrade to the executive floor, provided there was availability. Prepaying simply takes the game-of-chance out of the equation. I have chosen not to pay and see what happens.
At the time of booking, the executive floor rooms at this hotel are $50 more that the regular rooms. Booking a regular room and then taking the $40 upgrade saves $10. I do not expect too many will pay $40 if they were not willing to pay $50.
I do not see this as diminishing my benefits.