OK, I'm slow. When I finally figured out this rolling tier thing, I was on the downslope from some heavy travel a year ago. Bottom line is that I can qualify as a Diamond with 5 nights before the end of August. It'll get harder after that and my anticipated travel won't get my close. So, since the lowest rate I can find in the area would cost $450 for 5 nights starting tomorrow. I know the T&C says you don't get credit for a guarenteed but no-show reservation. I'd go check in and point out that I may or may not get back each night (nothing in the T&C says you actually have to sleep in the room that I can see). Might go ruffle the bed at the mid-point and then go back and check-out. Besides the Diamons qualification, I'd get about 5500 HHonors points, 550 United miles (Hampton plus credit card), and a free snack

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Is it worth it for Diamond? Seems like that mostly gets an extra 25% HHonors bonus, the ability to get a last minute reservation (can't think of any time recently when this would have mattered), and higher priority for upgrades. My personal and business traveling is at the Gold+ or Diamond- level in terms of stays/nights. My instinct is no. Convine me otherwise if you think I'm wrong.
Thanks.