Figured out my earlier issues, but did people ever figure out a solution to when the Katerina house event never fires? I'm not using any mods, manually sleeping, but after the day when you talk to bill and chris and agree to leave for Katerina's next morning in his range rover, nothing happens.
Edit - so apparently for those who were stuck on the Kat visit- it's so weird, if you talk to bill about kat, then do nothing rest of day and sleep, it works properly. If you talk to Bill about Kat, then talk to Chris about the visit (which you're normally supposed to, the game has dialogue for it), then the morning event doesn't fire.