I just recently booked at a Hilton Hotel and was given some upgrade options for a fee at time of booking and then again via email at a later time. Is this a waste of money even though the paid upgrade options are cheaper than the cost of selecting that type of room when initially booking? And do hotels that do this don't bother upgrading you even if you have status but you declined to pay for an upgrade? Since I'm already getting free breakfast (Great Getaway promo), should I go for the points or do I have a shot at the free room upgrade? As HH Gold, I know I can select either: 1-Receive a space-available room upgrade, including breakfast. 2-Earn 1,000 Hilton HHonors® bonus points per stay. With eStandy Upgrades, I was given the option to pay for: $5 High Floor Request, 11th Floor or Above $9 Pool View Request $15 King Bed, PURE Room $19 1 King Bed Disney View, PURE Room $19 Connecting Door Request $79 Waldorf Deluxe King, 448 sq. ft. $129 Waldorf Deluxe Suite w/ Balcony, 945 sq. ft. $139 Hilton Suite, 1,255 sq. ft. $199 Waldorf Luxury Suite, 1, 460 sq. ft. How eStandby® Upgrades Work: 1 Select each eStandby® opportunity below that interests you, then click the "Continue" button. 2 Find out at check-in if you are awarded an eStandby Upgrade® or any combination of Xtra Offers. IF YES You agree to pay the additional amounts stated below for your award(s). IF NO You will stay in the room you originally booked and pay nothing extra. I also realized that some of the options included upgrades to the neighboring hotel. Does that mean if you have status, you would normally be considered for upgrades to that other better hotel?