The thing is there's nothing else that's teased to happen in the next update other than that and we're already in December. And I'm not sure Cari would be keen in making a 2nd update in a row where time hasn't advanced significantly, especially when he mentioned on Discord that Orion, Annie, and Chang were going to stay in Kredon for the whole school year and we tentatively have about 5 updates left until the story ends.
My personal guess is that Christmas event could happen as the finale for 0.9, while Caly trip could be like the New World event in this patch where we spend a huge chunk of it getting to know knife-ear culture and possibly getting some much-needed infodumps about stuff like the gems or Orion's powers or how Caly got imprisoned. Luna event could happen somewhere in the middle, possibly an event where Orion drags her in Eternum for something. Christmas tho could definitely open up a lot of scenes like Dalia x Annie, Annie x Nan, and/or Penny solo, so it's definitely something that Cari ought to consider.
Edit: Also just for the lulz it's possible that Caly event ends with Orion and Caly trying to get back to Eternum...but our horndog of an MC will overshoot and both will end up in Kredon instead.