Has anyone upgraded recently?
Yes. I try to upgrade my outbound flights. I will only upgrade my return flights if there is a great deal.
What route and cost did you have?
Route: I fly United from Denver to and from Munich, Frankfurt or Heathrow for my international flights.
Cost: varies significantly. I watch upgrade prices very (very) closely and upgrade when I see an "offer" that I like. I see prices that vary by as much as several thousand dollars for a one-way upgrade to Polaris. During the period of time when business travelers might be booking, upgrade prices seem to be at their peak. If there are unsold seats, prices sometimes drop as the flight day approaches.
Upgrade waitlist - I assume that United would rather sell a seat as a fully paid upgrade than the $425 or $550 that someone on the waitlist might pay.
Did you upgrade at booking, later online, or at the airport?
At booking - never, unless I get an upgrade "offer" at the tail end of the checkout process.
Later online - yes, usually
At the airport - I have never upgraded at the airport, on my flights, the premium seats were always fully allocated the day before the flight
Recent business class (Polaris) upgrade prices that I've seen (Denver to or from Munich/Frankfurt/London) have been:
$899 - 2025 upgrade offer at flight checkin (i.e., 24 hrs before the flight)
$742 - 2025 upgrade offer on a 4th of July flight from London to Denver
$799 - 2025 upgrade offer at flight checkin for a flight from Lima, Peru to Houston
$897 - 2024 day of purchase upgrade during ticket buying process (not selected during flight search)
$912 - 2024 upgrade offer 4 days after ticket purchase London to Denver
$1061 - 2023 day of purchase upgrade during ticket buying process (not selected during flight search)
Each of these upgrades had been priced at 2x, 3x and 4x at various times when I checked.
What do I mean by upgrade "offers"?
Essentially, an online price at any time other than during the initial ticket purchase, which might include:
During the checkout process
Any time after ticket purchase - look at the seat map to see what an upgrade would cost to any seat on any day; I've seen prices swing by thousands of dollars from one week (or even day) to the next.
During the checkin process for the flight - on occassion, I will get an "offer" to upgrade during the flight checkin process, though I think that these may be rare and based on my status as United Gold.
My recommendation is that you must be willing to fly the seat you have purchased because you never know if you'll see an upgrade at a price you like. And don't panic and pay thousands during the peak business pricing times.
This experience is all based on flights to and from Denver, a busy United hub.