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.
"Canon is only important to certain people because they have to cling to their knowledge of the minutiae. Open your mind! Be a Star Trek fan and open your mind and say, 'Where does Star Trek want to take me now'." - Leonard Nimoy