Sometimes (most times?) the tie-in writers are better about this than the folks who made the show/movies. I still get annoyed that when Kirk said, in Star Trek V, "I lost a brother once," nobody thought even for a second that he was talking about George ("only you call him Sam"...).
Nowhere near as bad as The Wrath of Khan. "I've never faced death. Not like this. Not even when I lost my best friend Gary, the love of my life Edith Keeler, my brother Sam and sister-in-law Aurelan, or my wife Miramanee and my unborn child. Oh, and the first two of those died as a result of my own actions, but no, I've never actually faced death before."
I actually interpreted the "I've never faced death like this" thing to mean this was the first time he actually was with someone he cared about throughout their dying moments and moment of their death, which really isn't the case with a lot of those examples. Most of the redshirts killed under his command were usually killed instantly before he could get to them. Gary Mitchell was killed after a huge boulder sealed him into a grave, so Kirk doesn't really witness that even if he did cause it. Kirk specifically looked away and avoided dealing with Edith Keeler's death. Sam was already dead when we see him. And I guess whatever relationship he had with Aurelan or Miramanee, watching his best friend of twenty years die was a bit different than seeing their deaths.
Or for another example, imagine a military officer who has faced death in some manner all his life and career. He's killed enemy soldiers, witnessed the deaths of soldiers he's served with or even commanded, including some friends. Family members have died, perhaps even his pregnant wife and unborn child but for whatever reason he was never on hand at the moment of death. Sure all these deaths take their toll on him and shape him in some manner. But then his best friend is fatally injured and he spends time with his friend on his deathbed. It's this that makes the officer of this narrative feel is the first time he's actually "faced death."