I'm a bit disappointed at the lack of an updated demo, but these things happen.
I hear you on RPG Maker being messy- I really wish it was built around string keys instead of numeric indices. I usually leave massive gaps in the various lists, but even that sometimes isn't enough. Reworking a game to clean that up sounds painful. I commend your commitment here- I don't know if I could get back to a project if I had to rebuild the whole thing over again.
VN-style character graphics are definitely an exciting change. There's a lot you can do with them, even without getting into animation and such. Limiting the poses to keep your sanity is a smart decision for sure.
I'm not entirely clear on the interactive life sim events- is this being able to choose the level of effort, or something beyond that? I thought it already had the former, but maybe I'm thinking of an update you posted on Discord.
Once again, I appreciate that the devlog has both regular updates and a concluding entry that summarizes the overall progress. I only skimmed the progress updates, but the continue-it devlog covers the new stuff pretty well.
Excited to see where this is going for sure!