pinniped

Given the state of HH points and how little Diamond status is worth, I can't possibly see how the math on this would make it worthwhile to do this even at an attractive room rate. I put very little faith in the future value of HHonors points. Everybody who has participated in this program for more than a couple years has been through multiple major structural devaluations - substantially more change and devaluation than Hyatt, Marriott, or Starwood have had in the same time period.

I've done my share of weekend stays over the years to top off a promotion or status requal, but 20 nights?!? $1000+ cash out of pocket, if not more since the UK probably doesn't have a lot of ridiculously-cheap Hiltons?

I'm sitting on 1.5 million points and Diamond status right now and I wouldn't pay much of anything to add to it. I'm probably going to draw down the points as much as possible in 2021 on an Asian trip just to get out of that balance before they devalue again.

Given that Hilton is going to continue pushing promotions and attractive room rates in 2021, and hopefully international travel restrictions will lift by then, wouldn't you rather save the cash and take advantage of promos when you actually want to enjoy the stays?