'Shadow Lord' is one of the very few Star Trek novels I've refused to read again. It's been ten years or so since I did, and my vague memory of it tells me that my opinion of it was that it felt like someone got contracted for a Star Trek novel, but had no intention of actually writing one, focusing on their separate idea and characters, while having Spock and Sulu tacked into the story and making arbitrary remarks in order to keep the Star Trek logo on it.
Honestly, that doesn't bother me that much. After all, TOS was made at a time when anthologies were considered the highest form of dramatic television, and so -- like many other ongoing series at the time -- TOS was designed to be essentially an anthology with continuing characters. Its strange-new-worlds format was deliberately selected to allow throwing the characters into a different kind of story every week. A tense submarine-warfare drama, a comedy-fantasy with Alice and the White Rabbit, a gangster story, a Roman epic, a Nazi story, you name it. So there was never meant to be a single, narrow definition of what "a Star Trek story" felt like. The format was intentionally created to accommodate a great diversity of genres and subject matters. Shadow Lord is Star Trek as a Meiji-era samurai epic, and that's just the sort of thing they might've done on TOS if it had been pitched to them, although their version would probably have been a lot more stereotype-laden (and would've gotten the Prime Directive right).
This post almost makes me want to read Ship of the Line just to see how bad it is!
Morgan Bateson getting command of the E-E, his entire command crew is the crew of the old Bozeman, and they are all male, even though what we saw in 'Cause And Effect' clearly showed us two female bridge officers.
Also the Typhon Expanse being a settled, routinely patrolled border territory of the 23rd-century Federation, when in the episode it was uncharted territory in the 24th century.