I hope this doesn't make me sound like a terrible person, but I can't recall any Trek book even coming close to making me cry. But, to be fair, that's pretty much true of any literature. For me, only music, or a very poignant scene in a movie, can get the tears to come; I've yet to cry after I've read something, even though I find some books amazingly moving in their own way. I guess my waterworks tend to be more aurally/visually triggered.
While I am simply too macho to cry. No, but seriously, I'm pretty much the same way. I've never been moved to tear by a piece of literature; there just isn't enough immediacy to the medium, not for somebody as emotionally shallow as I am anyway. On the other hand, "Luck of the Fryish" gets me to tear up every damn time I see it.
Fictitiously yours, Trent Roman