Reverse situation applied to me about 10 months ago. Although number of nights are far less - about - 75.
Diamond is a cut above most other programs I have been in including Marriott. Travel worldwide and use about 8-10 free nights per year. Bus and pleasure. Have never been denied using points even in NY or London. Could be just lucky however,batting 100%. When I have called the Diamond desk to get point rooms,also batting 100%.
When using points I (we) have been treated the same as when we were paying,even in high tariff locations such as NYC ,Tokyo,London.
Upgrades--again almost 100%.
If you have a problem they will take care of it imm.
DMs are sent an E mail after they check out to ask if there were any problems. On those rare occasions where there have been,the general manager has called me directly with the cell on file.
What a lot of these programs may not know (or consider) is behind the elite member are in many cases large staffs and meeting planning decision makers. So it is not just simply the individual members # of stays/spend.
All things considered,myself and staff have choosen Hilton over the several other programs.
"1k Heavy"