Any recent data points on upgrades for a Diamond on a points stay?

About 3 years ago stayed for 2 or 3 nights - I think on award - no upgrade. It was King's Day week (which I didn't know about) so maybe that was part of it. Small room, no views.

Next month we have a 1-night and then a 5-night stay (mid-October). Points.

Yes, I know first-world issues. As mentioned above: breakfast, lounge and location great. We are fine with the rooms we've booked, just curious about our odds to get a nicer view. (Is it worth asking at check-in if a) not automatically offered and b) I see better rooms online/app?)

Thanks.