Or, just a thought. And this may be wild and crazy, but bear with me.
We focus on the short term, don't plot out every single aspect of each post a year in advance like you said, and also just toss a date on there to keep some semblance of continuity moving forward. Especially if, in season two, @Master Bruce gives a hard start and finish dates to go by. Times aren't necessarily needed, but a date, at least, is always nice to make sure things gel together and we don't end up all crossing the streams.
In open-world sandbox games that have various moving pieces, I find that to be the best way to maintain cohesion without future finagling.
If this were a structured RP with a handful of players, I wouldn't date my posts, either.
Not suggesting that this should be a mandatory rule by any mean, you all do what you want. But the whole "in the long run it doesn't matter so let's embrace timey-wimey narrative" seems odd to me. There are some things where stating in the long run it won't matter applies well, but I don't think this is one of them.
If the phrase "a bit timey-wimey" doesn't indicate to you that I was being slightly facetious, I don't know if anything ever will.