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?