Should I expect the second one to be coming up next, so replace both uppers now?
We're at 98,000 miles and the other feels ok but do they generally have a general set lifespan?
I put up a post about this very question some years ago and the general consensus is that they are worn out by about 150K miles. My right upper started going bad at around 122K, or rather, that's when I noticed it going bad!
Yes, you could do just what needs doing and not replace everything at once, did my hubs that way, about 20K miles apart. With a dial indicator you can test all four with a jack stand and floor jack, movement should be no more than 1 millimeter.
If this truck is a long time keeper, use GM OE parts. ACDelco Professional or Moog CK series are good for at least 50K miles and likely double that. If you're going to sell it tomorrow, Moog's RK series will save you quite a bit of money. Of course, if you're going to be running baja races with Ford Raptors, I doubt even the best will last that long!