Figured out the issue.
Apparently I'd progressed some of Kana's storyline, so after the laptop scene, it immediately shifted to progressing the next part of Kana's story rather than the next scene for Veronica/Madison's. Which basically left Veronica/Madison's storyline effectively broken.
Viewing post in Corrupted Kingdoms (NSFW 18+) comments
Unfortunately I've already since saved over the save file in question after loading up and trying again with an older save.
If it helps though, the Kana event in question was the one where you're woken up and told that she's gone missing (her heat event). Best I can guess, the disk part ended and allowed the Kana event to activate instead of immediately going to the TV part.
Sorry I couldn't be of better help. Didn't think to keep the save.