Regarding the saves:
Whenever possible games should be developed in chronological order, having to restart for each update kills interest in a game project really quickly.
But.
If if the game is unsatisfactory to you to the point where it needs reworking, that should be done as soon as possible because the further along a game is, the worse having to start over with a new save is. So it is probably better to focus on fixing anything that needs changing in the existing game and getting that out of the way rather than trying to mix adding new content and fixing the old.
Regarding the changes/new content:
Christine is such a hypocrite if Daisy avoids getting drugged at the party. She doesn't want to fuck despite being a massive slut, but it was just fine her doing that to the faithful wife? A "karma" route where Daisy avoids the traps set for her and instead watches Christine falling into them instead would be fun, I think. Especially if she learns to enjoy watching Christine getting punished. That could be another manifestation of "corruption" I guess?
The college reunion of flashbacks is an interesting choice, I'm not quite sure what to make of that. Is this introducing new characters that Daisy is going to interact with again in the present? If not, the scenes are hot but it doesn't really fit into the story.
And Jessica initially objecting to fucking but then letting the boys gangbang her just because Lana said so makes me wonder what exactly the relationship between those two was like?
This apparent "going to Hawaii with a random guy from her class" thing that seems to be happening? Seems like a really stupid twist, makes the cliche blackmail plot seem reasonable. Who in their right mind would go on a trip like that? Even if he hadn't molested her when they were dancing?
One final thing is that you really need to pay attention to filename case, computers that don't use windows have case-sensitive filesystems, "Jessica0.jpeg" is not the same address as "jessica0.jpeg". If the game is looking for one, but the file is named the other, then it won't be able to find the image.