UK only comment. I use my Diamond status mostly for UK. When I have been offered a 1 or 2 cat upgrade at check-in I politely show them the Diamond benefits page that states if they have a suite I can ask for it. .
Benefits and Member Tiers with Hilton Honors. They have then 'checked with their manager' and been upgraded from a standard king to a junior suite or king suite in a few properties. I understand this may not work in the US but I have, so far, a high success rate for suite upgrades. Hope this helps others.
Alison