That's where the current main story ends.How do I know when I've caught up? Just seen Anna's boobs after the corset scene and seemingly don't have a way to progress unless I've missed something. Tinks asked for a winter hat but I have that and nothing's happened.
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If you want to confirm that you've completed everything available, you can check for locked images in the gallery section of the office computer (Quest & Data Images). You can also check all quests are completed via the screen between your bed and the computer.
There unfortunately doesn't seem to be a way to check that you have all outfits in this version. Nor does there seem to be a way to change Tink's outfit to anything but the most recently created one. I'm hoping Salty01 will add that in the future.