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.
I agree that it would make more sense for TWOK to be placed in March 2283, assuming Kirk was born in March 2233. TSFS follows in April/May (not more than a few weeks later), TVH in July/August (3 Months later) and TFF a few months after that, at most. However, I think the Okudas shuffled the dates to allow for the claim that the UFP/Klingons/Romulans founded the Nimbus III colony jointly 20 years before. Since there had been no contact between UFP and Romulus between the Earth-Romulan War and Balance of Terror, this must have happened after Balance of Terror. Personally, I think there are better ways to reconcile things, but that is what they did.
totally agree looking at the dating for TFF the logical reason is that it has to occur after not only "Balance of Terror" but " Errand of Mercy" also ( which they set in 2267) That said I think there is an over emphasis on dialogue being exact as opposed to vague. If Spock says something, I will take it as accurate, others... not so much. either way the TFF dating simply jars.
As an aside, I would further defend the 2283 dating of TWOK as saying that Kirk met Antonia while based on Earth and his return to Starfleet, would be him choosing NOT to retire just after TVH ( admittedly this assumes some sort of break between the saving of Earth and the hearing, though its hard to imagine under the circumstances the hearing was top priority).
I guess if we take 2267 as the baseline for the creation of Nimbus III then based on 2283 we are looking at 2284 for TFF ( at best) and it would have been 16-17 years it was set up, so Caitlin's comments are vague but IMPO not irreconcilable.
As a further commentary, looking at the Okuda timeline, I find the idea of "gallileo seven" as the first story of 2267 unlikely as well, given " Charlie X" is set around Thanksgiving and "Dagger of the mind " is set after christmas ( or after the christmas party anyway!) they seem to cram a bit too much into the post christmas period.