DH did diamond challenge years ago and was hooked on the benefits and priviledges of diamond status. Over the years Hyatt has treated us very well and we've gotten used to it. Initially there were also offers where stays would add up for free nights (FFN) so hopping around would get stay credit as well as gaining free nights (vs using points). Unfortunately those days have been gone for several years now. In the begining of the year DH has a bit of travel, when there's two Hyatt brand hotels he will hop between two (especially if pricing is close)... thus picking up stays quickly. This helps chip away at the 25 needed to requalify... some times we have been traveling where there isn't a hyatt option... so come september or so start accessing what will be needed to top off the account earnings. This year he requalified for Diamond on stays first and then almost a month later, with nights. This was the first time for him... he had a long stay in Germany and was using points & cash. -- which gets the stay credits as well as reducing the actual spending.
He now travels on our dime for business so he has to access the spend vs options. As usual, right now he's got 5 stays done for year (and 6 nights). This is typical for January... but February will probably be just spending Chase free nights & and using points since the nightly rate is high.
Good luck
Carolyn