I dunno... this was something that occurred to me when I saw Generations in the theater when I was 22. I saw Scotty watching Kirk die at the beginning and thought he'd have something to do with him at the end. Obviously, I was disappointed.
Then have you read Engines of Destiny? I haven't read it myself, so I don't know how satisfying it is, but it does play on that basic premise.
Walter Koenig's outline is too depressing. I am a huge fan of Mr. Koenig, but I think the tone is all wrong. Who wants to pay to go to the funeral of a friend or in this case several friends?
I have mixed feelings about this. I kinda like big epic movies where a lot of the main characters die or are wounded (the Magnificent Seven is a good example), but I'm not sure if I'd like it as much in Trek.
The Kirk character was at his best beating the no win scenario. I totally understand that in real life people die, but in ST Kirk at is a symbol of overcoming the impossible. Why insist on killing the larger than life hero?
That's basically the mentality that went into the Shatnerverse books, to fun, entertaining effect (though YMMV, of course). But, I can see it both ways. Even the heroes gotta die sometime. I think he would've liked to die with his boots on, but I remember one time in an old discussion here, someone suggested an alternate ending where Picard goes down to fight Soran, and Kirk takes the center of the D to fight the Duras sisters, and I think that would've been pretty freakin' cool. But hey, that's life. Oh well.