I've read a lot of trip reports and posts here from people who mention getting a room upgrade upon check in. I have always wondered, do you ask for an upgrade? Do they just say "Surprise! We've upgraded you to a ___ room!" We are staying at PPH and DLH next week (!) and I'd love to be upgraded, but I don't want to appear greedy or high maintenance.
I, too, have also noticed an abundance of upgrade stories lately - especially at the Paradise Pier! I was the lucky recipient of one such upgrade last December - and honestly, in all of my onsite stays over the last 23 years or so, I've never been upgraded at any of the hotels until this past December! I had read about it happening here and there, but I was just never lucky enough. So I can't say that it happens easily, from my own personal experience, but it does seem to be happening in a wave lately, doesn't it?
Anyway, when I got my upgrade to park view at PPH, I did not ask for it. I simply showed up early for pre-check in. Very, very early. Literally, before sunrise. I was the only one at the front desk checking in and there was no one around in the lobby. So the CM handling the paperwork basically said, "You've been upgraded to a park view room," and "Your room is ready now!" (Those are two sentences you
want to hear when you check in anywhere!

) I went upstairs and watched the dawn break from the window, and then anytime I was in the hotel room over the next 3 days, I was obsessed with staring out the window at DCA! That view kept beckoning to me!
I think other people have tried to ask for upgrades. Sometimes it may work; sometimes it may not work. I suppose it largely depends on timing and the particular CM who checks you in (some of them are friendlier than others). I can't help but think that the chances might be higher for upgrades if you show up well before your official check-in time, as early in the day as you possibly can. Once people start checking in or showing up in droves for early check-ins, more rooms of all types will be booked up.