I am going to add on an extra night in NYC in December, leave the kids behind, and take the wife to see NYC at Christmastime for a couple of days.

Work will pay for two of the nights; third will be on me. As a Diamond, is there any reason to book the paid room versus the reward stay for the first night, or vice-versa? I know in theory award stays are to be first for upgrades, but I've personally never experienced that.