I agree with you that some of the girls just... don't seem aggressive enough in how they're presented to be a boss battle. Like... Nile and Misty? I look forward to the date/story content, but they don't feel like they have that *end stage boss* vibe.
I am glad that you're planning to go over the Security Office with a polish pass later. The gameplay is enjoyable, and the the scenes, etc, are great, but it still feels like it's missing something - like it's not as polished as the Nightclub, and I kinda feel like it's because of that lack of explanation of what the place is, why we're guarding it, and why the girls are there every night. And that honestly makes sense, seeing as you were basically starting over whole cloth when you made it.
Looking forward to what you guys have coming up over the coming months. You've already come a long way since you started this project all those years ago. You should seriously be proud of all you've accomplished.