Thanks for new content, it's great!
The only thing I would think needs improvement, is the transition at the end of chapter 5 if you choose to "Handle it yourself". It's a little rough and doesn't really explain why Raynare dissapears the same way as if Rias destroys her.
Perhaps a couple of extra frames and/or dialogue in that choice, before the cloud of feathers, would smooth it out and make it feel more natural. Even a black screen with some text that says something like, "After that, I was ready to move on and killed Raynare with my own hands", it'd at least explain why she dies. Or some extra line during the deed that says that "devil cum is as poisonous to fallen angels as light spears are for devils" (although that would raise some questions about Akeno, so maybe not exactly that).
Other than that, the rest of the update is very organic and feels like it's following the nature of the characters. I'm digging the new sandbox mode as it makes for an experience more similar to classic dating sims, and it seems like it'll be a great way to implement more content for other girls in the future (maybe we get a school location and some student council fun?). Endless possibilities, I'm really excited about it. Thanks again, and specially for providing it for free