I don't often ask for late checkout - but the few times that I have its been quite difficult - 1PM isn't usually a problem - anything later seems to be a struggle.

While it would be great if the Gold Passport Concierge takes a more active role on Flyertalk, I'm sure that's a corporate decision. That said, I do know that she helps out many of us (including myself on a couple of occasions) behind the scenes. Hyatt's program is a bit less complicated than Starwood though.