I like the rolling system
I am in Higher Education and my travel goes in cycles. Some months, I have a lot of travel out of the area and others I do not. With the rolling system, I don't end up doing 'hotel runs' in order to maintain status. It is amazing to watch the airline mileage runs at the end of the calendar year. With HH, I don't feel that need.
Most properties I have got extremely good treatment as a Diamond member. Only once in St. Louis was I informed that used a lottery system to reward elite members. Not staying there when I return next month. What is surprising is the range of rewards - some hotels have private rooms for that free breakfast, others you get a full breakfast in the restaurant. I have been at some that provided free booze during the cocktail hours and others nothing.
At one property in Florida, I got a large two room-suite with balcony overlooking the bar. At an Embassy Suite in California, I got a two room suite that was like a Presidential Suite. And then there has been the other end...... the upgraded room looks just like the regular room except a couple of bottle of free water.