The agent Lisa and I spoke to when we tried to get the 2nd upgrade was aware of the situation, and didn't offer a thing. So did the first agent I talked to after upgrading Jeff, when I called to find out the other locator# Perhaps Jeff will have luck at check-in in getting what frequent travelers call an "op-up" (an operational upgrade at the gate not supported by any upgrade instrument or currency.)
Lars, I understand what you're saying but United is very much not disposed to do anything special these days. From firsthand experience just a week ago, when I canceled a business trip due to my just-broken shoulder and wanted to reschedule it, they wouldn't even waive the $100 change fee for an elite member, and had no interest in the note I have from my doctor saying I shouldn't fly for 2-3 weeks.
Also, flights on all airlines are far fuller these days than just two years ago. They've all cut back on number and/or size of planes on each route and are filling them to capacity. It's rare to have even an empty middle seat next to you, and that's supposed to be a United Premier Elite benefit when at all possible. Plus that's after all us elites have rabidly been diving for F upgrades we feel "entitled" to, like a fresh line on a powder day - F is always full with higher status elites, Coach is packed to the gills, and if someone without status tries for an upgrade they're usually not even available for sale.
Lars, I think you got lucky (at least with the flight, the accident was horrible) when UA upgraded you all. It absolutely isn't policy. I would encourage Jeff to call them arranging for seats, wheelchair, and asking if there's any way they can sit together in first. But that's much easier now that they already have one seat confirmed in first.
The days of the airline agent upgrading a family or a couple just because there's an injury are long gone in the US airline industry. And I'm not bashing UA - I think they're the best of the bunch overall, that's why they get most of my (and my client's) travel dollars. Plus the Chicago to Albany leg they're on is a BarbieJet with a tiny First class - only 2 rows of 3 (1+2) seating. Those are hotly contested for by elites who have "the right" to an upgrade under most circumstances. I figure let's improve the odds by locking in at least one of those few seats by using my miles.
It's just miles
(It's not as if I'm not scoring 26,000 miles just a couple of months later from one trip to Germany on a $321 ticket!)
PS - Ironically even my having the miles is as an indirect result of Epic. I thought I was pretty good at the FF game but then ElkMtnSkier introduced me to FlyerTalk.com a couple of years ago. I probably scored 3-5 times the number of miles I normally would from frequent traveler tips I learned over there.