If you are staying at a swanky place then you are more likely to get an upgrade with points in my opinion. But only because you used points to stay at these places in the first place. So perhaps it is just that you stay at them with points more often then not?

To further this idea. Say you stay at less desirable hotels during your work stints. Think Residence, Fairfield, Springhill, Townhome, etc. And everyone else who it's at that convention is also racking up points and status on the company dime. So you are competing with 50 other elites who possibly outrank you or match you. And the hotel has 250 rooms with only 30 suites. If you didn't check in before everyone else and you didn't ask before everyone else, you know the answer before you even get there. This is why chatting with the hotel before you get there is now almost essential when staying at a lower rung hotel.

Edit: forgot to mention that lower rung hotels are often run by lower rung affiliates. So their front desk personal are taught well on how to deny a guest an upgrade. "Oh, sorry sir, but you booked with points and we only upgrade paid rooms since we are such a small hotel with fewer suites." You might hear that and go, sounds legit! And be done with it. You might even think it's an actual policy and stop asking for upgrades when using points. $20 at lower rung hotels often gets you an upgrade even if you are gold status. $100 at a swanky hotel can do the same. Or a crisp $50. People always like $50's for some odd reason. Perhaps because they only get them in birthday cards, Xmas cards or as graduation gifts?

Contrast that with a destination hotel with 400 rooms and 150 of them are suites. Sure, many guests there will have status, but many will be on par with your status. So instead of getting a room from Friday to Sunday you get Thursday to Monday. Now you can check in via the app on Wednesday. The same day the elites are checking in for their Friday stays. You chat with the hotel and you ask about spa reservations, the to do in the city that are unique to that city and, oh, if there are any upgrades available this is my 20th wedding anniversary so it would be so very much appreciated. If not, that's okay, thanks for the tips on the town and checking for us. So looking forward to our stay! 🥳

Why leave on Monday? Because 80% of the hotel is leaving on Sunday and 60% beat your status. So Monday. When I did this recently at the Laguna cliffs Marriott I got a suite for the price of a crappy room (well, nothing is actually crappy there, but you get the idea) and a late checkout at 4pm confirmed on Sunday night through the app. I also got a nice card wishing us a happy anniversary, two bottles of Cabernet, a cheese board and $100 credit at the spa. Not bad. At the time I was platinum status.