Thank you for the extensive post!
1.
When you are on a manual save slot grouping. It is saved based on the slot position. This is to imitate renpy saving while still allowing better features like sorting. So if you would have saved slot on position 15. Every slot would be filled with 'new save' up to 15'th slot.
When you are on another grouping type it should be by date order only.
2.
Yes, I'm looking for someone who could draw a map in a sort of colorful but clear style similar to the current overworld map. Yet at the time, I couldn't find anyone, so it was postponed. If you wish to suggest someone direct message me on discord
3.
More additional information will be available on the tracker in the update approaching as I recently worked on this. But you already know this through discord :3
4.
I'll add to specifically disable click sound to to-do list.
Thank you for playing and taking the time to write this <3