Hmmmm... Upgrade Email
 

I could never understand why on some upgrade emails I get the diamond upgrade at $0, and some I'm being offered to pay.

I think I've noticed a pattern in my limited experience.

I recently made 2 reservations - one at the MCO Hyatt and the other at the Grand Cypress.

MCO Hyatt treats their diamonds very well, and their upgrade form shows it - the upgrade showed at $0.

At the Grand Cypress my upgrade form showed $9 for the upgrade.

It's no secret that this hotel has always been problematic with upgrades and either the front desk needs retraining, or they intentionally don't give diamonds their benefits without asking for them. They probably did this intentionally. I swore I wouldn't stay again here unless it was a big savings over my other choices, and unfortunately, it was a big savings :) So, I guess I'll be armed at check in with their room availability to make sure I get the best available :)

Has anyone else run into this with other properties?

I've wondered the same thing but never thought about it the way you did. I'll keep an eye out when I make future reservations. :)

I have received these as well. I received them from the Hyatt Waikiki which has always been great about upgrading us. My thought is this is just something that is automatically sent out to anyone with upcoming reservations.:)

That doesn't explain why some properties show the room upgrade at a $0 cost for diamonds, and others show each different regular room upgrades with a price.

IIRC, Waikiki shows it with a $0 - but I'm not 100% sure. I always get a great upgrade there too.