Thanks for all of the suggestions, even if my original post wasn't crystal clear in stating that I was getting cases that were trimming shorter, rather than longer. It turns out that the issue was caused by two things.
First, some of my cases's shoulders were pushed back farther than others, including a couple of the "too short" trimmed cases. When I gauged them, I didn't pay enough attention to the way the heads of these cases went a little too far into the gauge. I'm using a Dillon .223 gauge, and the max/min ledges are nice and clear, but I was only paying attention to the cases not being unsized or not sized enough. I'm sorting out those cases, with an eagle-eye on which ledge each case meets or misses.
The second issue was definitely those coated gloves. I thought they might be an issue when I had the trimmer's switch catch on the glove and not go all the way to the Off position. It looks like sometimes the glove would get in the way of pushing the case all the way into the case holder, so it was the glove stopping it instead of the case holder's stop. Other times, the glove was out of the way, and the case went in fully. Without the gloves, I had a much more consistent feel for when the case was really in the holder. The glove covering my thumb and index fingers clearly changed things, but only on an intermittent basis.
This afternoon I backed the case holder out about a full turn and started adjusting in small steps. I put a Sharpie mark on the case holder so I could keep track of how far I'd turned it. And I held the cases carefully, near the head, and with only my fingers. Once I got the case to contact with the cutter head, I used the caliper after each little adjustment until I got to about 1.752 or so. Then I trimmed several more cases and calipered each once it was trimmed; they're all staying within 1.748 - 1.752, and I'm happy with that. To finish up, I locked the die lock ring down tight (I use Hornady's rings), and made a pair of Sharpie marks on the case holder that line up with the 3:00 and 9:00 witness marks on the case holder mount. That should make it easy to repeat the adjustment later.
I will caliper the next dozen or so cases, and if they stay within that tolerance, I'll only caliper every tenth or so case, just to keep an eye on it. And of course I'll re-gauge everything to separate the "sized enough" and "sized more than they should be" cases. Those "sized more than they should be" cases really only have the shoulder pushed back a little more than spec, but combined with the occasional effect of the gloves not getting in the way, they really messed with me.