Then again, why assume he was referring to Earth years? Klingon years could be shorter. (Although the novel continuity has unfortunately established that a Klingon year is just about exactly equal to an Earth year, since the numerical difference between the "Year of Kahless" and the Common-Era year is identical in both 22nd-century and 24th-century tie-in fiction.)
Add to that the changes from the first pilot to the early production shows and I think it's better to take TOS as a single entity instead of season by season.
Umm, the
first pilot? "The Menagerie" established that those events took place 13 years in the past.
This side of paradise lasts over two months with the retreat to the planet taking 59.223 days alone.
You mean "The Paradise Syndrome."
The idea of spreading out the TOS era is not without merit, but it's difficult to make it work in practice. As I've said, the overall consensus is that we have only 5 years to fit all of Kirk's pre-TMP adventures into. The animated series is pretty clearly set after TOS, since a number of its episodes are sequels to TOS episodes and there are changes to the layout of the ship (a second bridge exit, a rearranged main engineering) and its crew composition. And if you want to include novels or comics, again, most of them are specifically written to take place after TOS.
Now, if you could justify an extra few years after the "5-year mission" to fit those novels and comics and maybe TAS into, that would be great. I'm sure you could make it work in a fanfiction context. But CBS Licensing wouldn't go for it. Everything pre-TMP has to go in the span of 2266-70, and just about all the tie-ins are meant to go after TOS ends. So the most feasible approach is to fit the three seasons of TOS into the first three years of the 5YM, leaving two years for TAS and whatever tie-ins you choose to count.
The consolidated continuity of most modern Trek lit works well in many ways but it also can work against creativity. When it comes down to a choice between fitting into the larger narrative and telling a story that doesn't fit I wonder how many people would try to wedge it in anyway.
There is certainly room with Trek Lit for telling stories that don't fit the primary continuity. A prime example is the
Crucible trilogy by David R. George III, published to celebrate ST's 40th anniversary. The decision was made that the trilogy would be grounded only in the events of screen canon and would develop things in an independent direction without regard for the main novel continuity, so that it would be accessible to readers who were unfamiliar with that continuity (because such a special anniversary event could and hopefully would get picked up by more people than the regular readership). So there are a lot of things in it that contradict what the novels have established, such as when Admiral McCoy dies and what the nature of the
Enterprise's post-TMP mission is (although it still puts TMP in 2273, because it still had to remain consistent with canon as CBS Licensing defines it).
The novel series by William Shatner and Judith & Garfield Reeves-Stevens, the so-called "Shatnerverse," also struck its own course independent of the primary novel continuity. In most of the books there's no blatant inconsistency, but the third Shatner trilogy (the "Totality trilogy") disagrees with the novel continuity on multiple points such as when/whether Bajor joined the Federation, what the nature and timing of the USS
Titan's missions were following
Nemesis, whether Kathryn Janeway was alive after 2380, etc.
And there are still standalone novels being published that aren't meant to tie into the main novel continuity at all. The recent TOS novel
That Which Divides disagrees with my own
Ex Machina in explaining why Chekov was never seen during the animated series. And a couple of years back, there was a Pike-era novel,
The Children of Kings, that was set in an alternate continuity that didn't quite fit with either the Prime or Abrams universe.
The continuity among novels in the modern era has always been an option, not a requirement. It's something the novelists and editors chose to develop because they wanted to, and it's not meant to prevent anyone from striking a distinct course if that's what their story calls for. The only thing the books are required to stay consistent with is screen canon.
Sure, Sulu could be a Junior early on, perhaps with some sort of "frocking" or rapid but only partially official field promoting going on with his sleeve markings. That would only be expected of a ship that is returning from a failed mission to the edges of the known, having suffered casualties among the top officers. And while the very point of giving Sulu that nonstandard promotion would be to give him new authority, Tormolen could be giving the bitter commentary from the point of view that best serves his own interests.
