Strange. I've heard people report issues with the Ventire Folk that have been moved into the Beauregard Estate, which should hopefully finally be fixed in the next early access update (though the bad news there is that the bug is mostly that everyone there should be dead and the bug is showing them alive). I've never gotten any reports of there being a similar issue with the Nithercott Estate, though; I'll have to look into that. Thanks for the additional details!
Anne's quiz for the trophy is started by interacting with a book in Master's old classroom rather than by talking with her directly.
Trophy 34 involves you going to multiple Estates in basically all of the regions in western Commorance, it's not contained to a specific region.