I'm more of a 24th century man when it comes to my TrekLit, mainly because of my love for DS9 and because....well, I already know how things turn out for Kirk and company for the most part, while Picard and the rest are still continuing their adventures (though of course there are exceptions, such as Spock and Scotty continuing into the 24th century). However, I do love TOS (of course!), and was curious as to the period after the end of Season Three and before the Motion Picture. What would you say are the best novels, comics, etc. set in that period? Some of the Byrne IDW stuff looks good, but I haven't read it.
"Traitor Winds", part of the four book "lost years" (all of which are in that timeframe) is superb. I read it before the preceding books, you don't really lose much by reading it first if you so choose. The other three are ok but nothing special.
TAS was all over the place with episode stardates ranging from before Where No Man... to past TMP, if I remember correctly. Better to think of TAS taking place in an alternate reality.
Yeah, the stardates in TOS and TAS are inconsistent but as long as stories/elements are not directly contradicted (The Slaver Weapon, the USS Bonaventure) I don't need to think of them as alternate. CLB, for example, skillfully wove some of these episodes into Forgotten History.
Parts of Forgotten History take place in this time period, and the novel over all is amazing. The same can be said of the anthology Constellations. Of the four "Lost Years" books, I liked The Lost Years and Recovery. Leonard McCoy, Frontier Doctor was worth a read too. I would imagine most people around here would suggest Prime Directive, but I've not read it. Also, I'm told the old novelizations of TAS make some of the poorer episodes much better, and I love some of the better ones already anyway.
It doesn't make any sense to hold TAS's inconsistent stardates against it, since TOS's stardates were almost as random, and TNG's first-season stardates were pretty random too aside from the first two digits. After all, the whole point of stardates, originally, was to convey no real chronological information of any kind. The producers of TOS wanted to keep its timeframe ambiguous, so they deliberately made the time references meaningless placeholders, basically a numerical lorem ipsum. So the fact that they don't convey a consistent meaning shouldn't be held against them when they were never meant to in the first place. As for the original question, it's rather broad, because the vast majority of TOS novels ever published are theoretically set in the final two years of the 5-year mission. You might as well just ask for the best TOS novels. Although there is, of course, a divide between the eleventy gazillion books and comics set in the last two years of the mission and the smattering set in the interregnum when Kirk was an admiral and Spock was pursuing Kolinahr.
These days, TOS is generally treated as covering roughly a 4 year period, instead of three, or at least as covering the middle 3 years of the 5YM instead of the first three. TAS gets shoehorned in at the end of it, and the novels representing the era you're asking about tend to get shuffled in kinda willy nilly. There's also the "problem" of several books and comics each taking place immediately or shortly after "Turnabout Intruder", representing the end of the 5YM. The Lost Years and DC Comics' "Final Mission" are two examples, but both great stories in and of themselves. Really, the best thing to do is to pick up a TOS novel that seems interesting to you, or pretty much any of the DC comics with the crew in their TOS uniforms, and not try to find one specifically set at the end of the 5YM. That being said, Prime Directive is a good one, as are Assignment: Eternity and the aforementioned The Rings of Time. It's easier to pinpoint books set between TMP and TWOK, or between TFF and TUC.
Neither of those books specifically claimed to be shortly after "Turnabout Intruder." Indeed, The Lost Years is very explicitly not, since it's a continuation of the supporting-character arcs from J.M. Dillard's previous three ST novels, and also references the events of Diane Carey's Dreadnought! as having occurred sometime before. Conversely, Assignment: Eternity is said to occur right after "Turnabout," but never claims anything about being at the end of the 5YM. The only work of tie-in fiction I recall that was explicitly both right after "Turnabout" and right at the end of the 5YM was a Strange New Worlds 10 story, "Empty" by David DeLee. The Okuda Chronology also claimed the 5YM ended shortly after "Turnabout," dismissing TAS and the novels, but its conjectural chronology (which ended the 5YM in 2269) was superseded by VGR: "Q2"'s canonical assertion that the mission ended in 2270. There aren't very many DC comics set during the 5YM era. Mostly they were in the post-TWOK era, fitting in between the movies. The first DC series ("Volume 1") only had three fill-in issues set during the 5YM, #30 (with a movie-era frame), #38, and the final issue #56 -- and the first two were pretty lame. Also, #33 was a 20th-anniversary story that used time travel to cross over the TV-era and movie-era crews. Vol. 2 only visited the 5YM era once in its first 57 issues (the fill-in #16 by J. Michael Straczynski), but then did a 3-issue flashback to Chekov's first mission within a movie-era frame in #58-60, then a 5YM-era 2-parter and a second-pilot-era one-shot in #62-64, and then with #73 it abandoned the movie era completely and did: a 3-parter spanning Kirk and Carol Marcus's relationship from the Academy to the end of the 5YM; a pre-second-pilot one-shot; and a 4-part arc in the 5YM era, which was probably going to be the new status quo if the series hadn't ended with #80. Oh yeah, and the TOS half of DC's The Modala Imperative miniseries had a 5YM setting as well. So if you want comics set during the 5YM, you'd be better off looking for titles from IDW, TokyoPop, and Wildstorm -- or going back to the zany Gold Key ones from the '60s and '70s. But there aren't very many of either. Especially the latter category. That's basically just Probe, In the Name of Honor, most of The Rift and Captain's Table: War Dragons, and Excelsior: Forged in Fire. Plus most of DC's Volume 2, as mentioned above.
In general, I tend to stick my TOS novels somewhere during years 4 or 5 of the 5YM just because it allows me to draw on entire televised series and I don't have to worry about trying to squeeze my story in between two episodes. On the other hand, I had to set the framing sequence for To Reign in Hell after The Wrath of Khan and its sequels--for obvious reasons.
I love Barbara Hambly's Crossroad. It's set a few months before the five-year mission ends, and features (among many things) Chapel deciding what to do with herself when the mission is over.
Crossroad, Dreadnought!, Black Fire, The Lost Years and Forgotten History are all excellent novels set between TOS and TMP. They're not all in continuity with each other, though. The Wounded Sky and My Enemy, My Ally were originally set in a Star Trek: Phase II (not the recent fan films, the original planned continuation of TOS) -esque second five-year mission *before* TMP, with a kind of halfway refitted Enterprise. ME, MA was later retconned into happening duting the original TOS five year mission and then re-retconned into having happened post-TMP by later books in the Rihannsu series.
For the "Star Trek Logs" adaptations, Alan Dean Foster changed all the stardates, and gave a new running order for the episodes, adding new bridging scenes to make the three episodes per book run into each other - almost seamlessly - and the characters reference previous TAS adventures. Not airdate order, nor production order. If someone is reading the adaptations of TAS, the revised ADF stardates are the ones to use.
Well, Dreadnought! is directly referenced in The Lost Years, so those two are in continuity (specifically the '80s novel continuity); and Crossroad is alluded to in Forgotten History, so those two are in continuity (specifically the modern novel continuity). Black Fire, on the other hand, is off in a world of its own in so many ways...
Supposedly. The version in The Bloodwing Voyages didn't get rid of all the TOS-isms, though (in MEMA or in Swordhunt). It changed the ranks, but left in stuff like the TOS uniforms, Chekov being at navigation, and Enterprise not yet having the TMP refit. Post-TMP gives a more realistic timeline for The Romulan Way, so that's probably the way to go (and The Empty Chair is definitely post-TMP), but after so many years of considering them as being in the TOS era I find it hard to give that up!
Crossroad also references Mr. Mahase, an alien crewman who appears in several other Original Lit-verse books, so it's one of those rare books linked to both the old and new continuities.