By now there's a
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on their wiki which shows all the dates. Else I'd agree that they are probably aiming for Halloween, so they can introduce a bit of Halloween content as well.
This I feel is really interesting to take a look over.
You could see how the release dates lenghtened once the scope of each update increased.
Early on you have rapid-fire updates that add very little in terms of actual additions, only the basic things like characters which (while detailed) did not go after the layered body system that is now more commonly used but were instead full drawings and had very little in terms of interaction. Systems were put into place to track stats like money, your inventory - that kind of stuff.
Once this was in place he expanded upon that and worked more scenes and dialogues into it, still just giving small additions to dialogue and story parts or just introducing more characters before changing what and how to update: rather than doing tidbits here and there he was instead working on whole chunks in one big update respectively while also amping up the quality overall. This being either a characters revamp, like with Roxxy or revamps to locations like the School.
The bigger the area and/or characters scope, the longer the updates became because this is not just a linear path, but rather a whole interconnected web with locations and their respective characters in mind. Since it appears he wishes to put out entire character progressions/Location specific events playing out the updates turn out longer.
Just take a look at the amount of things done in the changelog for each respective update past v.0.14.5 - those changelogs become massive compared to the older ones: so big they even had to be broken down into their categories.
So, one can totally just go assume that the update cycle did get longer, because heck, they did BUT people need to also remember that the bigger updates still put in large amounts of additions that are befitting for the time invested for said update - some noticable on the forefront, some not so much.
While I personally enjoy having a nice big chunk to play in one sitting, this is now actually starting to grow too massive for my liking.