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Mindlessly copying guides from other websites doesn't work, if said guide is wrong. The office next to Woodman's is LOCKED during Automatic Love and cannot be opened by any means (checked on latest update 1.06)
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Also, if you go out on the balcony and shoot a ladder down from the above fire escape and attempt to go the the balcony (the one Judy takes you to much later in the game during Automatic Love), there is a static wall-fence to keep you from getting into Maiko’s office in this way either (seems like this was supposed to be “the way”, but was removed in order to progress Judy’s story more gracefully...