I don't get it. As a Plat I almost always get an upgraded room at HIs, Indigos, CPs and even HIXs when they have them. I always book the lowest priced King room, and at least get the best in that category be it an Executive room or on occasion a suite. One does have to remember that many HIs don't have much to offer. Some offer chits for drinks, breakfast and/or gift bags of crisps and granola bars.
Much is left to the discretion of the property and likely based on local competitive circumstances, but almost always I get the best room available in my category of something even better. This past weekend, I gave a friend two nights at one of the Point Break HIXs and she reported she got a suite. Another time I booked a room for a friend under my name at the Allerton Chicago when it was a CP, and she raved about the suite they gave her (er me). But I never have to email or call in advance to secure these upgrades, though I suspect the earlier in the day one checks in, the better the likelihood of better rooms not being assigned.
Last month I checked into the Ottawa Indigo, again using the Point Break for two nights. The desk clerk said she could give me a suite -- even on an award stay at 5K a night! -- but that room wouldn't be ready til later in the day. I'd had a suite there once before and enjoyed it as I had friends come by, but this trip was pretty basic and it didn't matter so I took the standard King that was immediately available.
May I stay at the right places, but maybe just once out of every 10 stays do I find myself not happy with the type of room I get put in.