if there is an update of this game, how would I update it and, what month of the school are we in as the game/story progress
You just have to download the new build and unpack it. You can feel free to remove the past build, saves are stored in a separate folder
Saves should be compatible with the newest build, unless for various development-related reasons the amount of changes in the build would essentially break that compatibility. Whenever something like this happens, we inform players about it on the dev journal
As for timeline, the game takes place over the course of the single year. It starts in early April and ends around late March (excluding epilogues, that is)
The timeline is roughly this:
Size 1, scenes 001-009 Early to Mid-Spring
Size 2, scenes 011-29 Mid-Spring to Summer
Size 3, scenes 030-49 Summer
Size 4, scenes 050-69 Fall
Size 5, scenes 70-89 Winter
Size 6, scenes 90-100 Late Winter to Early Spring
The specific start of the various sizes depends on the route, but this is the approximate framework for all of them. The time elapsed between subsequent scenes can vary from hours or the next day to possibly a full week, so they can't be pinned down to a specific calendar date (unless it is a holiday or a character's birthday).
If you're curious about the lore and more meta aspects of the game, we always encourage people to join the discord server where these types of questions and discussions are discussed with fellow fans and the development team . https://discord.gg/rgBEwRG6