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Just got the game this update. Literally in love with the game. I know that it won't be any time soon. But when will the next update be? Also, will progress transfer over into new versions of the game as they come out?

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I downloaded the demo, played through most of it, then sprang for the newest update.  My progress carried over just fine.  Like all Ren'Py games, the saves are stored in a separate folder from the game files themselves, so deleting the game folder and unzipping the newer version in its place is the way to go.  (Simply unzipping them on top of the extant installation is a good way to bug out a game - don't do this.)

As with any game development, the answer to "will my saves carry over?" kind of ends up being "it depends," simply because backend changes or major revisions can make using old save data difficult and artifacts from earlier versions can get baked into an old save.  However, at the moment, saves seem to be working fine.

One of my primary goals with every update is to maintain save compatibility (I'd rather increase production time than lose existing saves). There are times when old saves will miss new content (for example, I plan to alter and expand the prologue in this next version), but those changes will be noted, and will more than likely be available in the memory viewer.