I've had over ten years of Diamond Status now, almost all CON-US, status earned by heads-in-beds.

Three memorable upgrades:

1. Killer suite on a high floor at the Hilton Ground Zero in NYC, circa 2004. One night stay.

2. Killer suite looking over the Ocean at the Hilton Huntington Beach. One night stay.

3. Suite with comical decoration (black fixtures trimmed with gold, black / gold vertical striped wall paper + huge black & gold hot tub, which I had LOTS of fun in, with my GF at the time) at the Milwaukee Hilton. One night stay.

Anything else I've ever gotten has been trivial at best.

I'm currently on my 34th night this year (usually 3-4 day stays) and have gotten one upgrade. That was to the full breakfast instead of the continental at a property I stay at A LOT.