While I generally find the book well researched and a good read, sadly the TOS era timeline seems a but wrong to me.
Obviously the Okudas could not forsee the five year mission being said to end in 2270, but aside from that some dates seem just odd.
Of note to me are the placing of "Where no man has gone before" which seemed a little late in the day ( indeed until the remastered version there was no real evidence it was part of the five year mission, with the opening narration being conspicuously absent).
The movie dating always seemed odd as well, personally I would say that TWOK occured in 2283 on Kirks 50th birthday ( which seems thematically consistent, and that his comment about the date of the Romulan ale was sarcastic). Regardless even given the 2285 date, the dating of TVH and TFF seem odd being 2286 and 2287 respectively.
According to the timeline, Kirks birthday is in March, therefore TWOK is in march, with TSFS being shortly after. dialogue in TVH places it three months after the previous movie - so still 2285 and following from that TFF is set shortly after the end of TVH so again, 2285 ( you could make a case for 2286 ) but there is no way it could be 2287 as far as I can see.
would love an updated version though, and agree having the Abramverse in a chapter at the end would seem to fit ( though I am dubious of claims there were no changes in time prior to 2233, and personally believe Enterprise reset the timeline somewhat).