On the code side of things, coming from someone who dipped a toe in RPG Maker a little, it's also possible to create events on the map that will self-trigger upon entering the area, check whether the variables you use have values and then create and assign them default values if necessary. So a form of self-check if someone loads a game from older save. It can be tedious to write it, and later update it when you progress the development, but once one is done you can simply copy it to other maps and it should work. More or less. Or run those checks where they are needed. But the specifics of it will largely depend on what addons you use (for example the one adding quests to the game menu).Now, that's a common problem for games in development, especially here where many non-professional coders work with RPGM or similar engines. Downside is ofc that it's clearly not an easy problem to solve, but luckily others before you came up with some 'solutions'.
The solution I found sufficient for most games is a quick-start to the new content. I've seen something like that in the current version, but it's noted as "very buggy" in the menu and I can only guess why.
You could alternatively put a savegame into the release build which is at the start of the current content. At the current state of the game this should be no hassle, because we have no story branching or harem-girl routes. This works as a good compromise for those that regularly check out each update for the new content, I find.
Another workaround is ofc a 'hidden' cheat chest with an OP sword or something like that to reduce the combat grind for those that start from the beginning, but actually want to get to the later stuff. This can help reduce the frustration, because it's faster to get to the new stuff, while still having full control over all decisions and gameplay.
Those two workarounds are failry easy to do, but they help a lot intheir own way. If you want to do something more sophisticated, like the chapter selection that you're currently trying, I'm looking forward to how it'll play out.
Godspeed for this great tiddy-game! It really stands out from the rest of the stuff on this site.
It's not the perfect solution as it will extend the time you spend on the game without actually progressing development but it's one of the options.