Ok so from my experince so far trying to find the route triggers:
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fat, drunk guy: go to his house (left of bathhouse) in the evening and grab the porn mag from the ground
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Bob: grab the bra from the drunk guys home instead. go bowling with Aoi and when Bob shows up afterwards 'don't interrupt' them (?speculation cause I interrupted and that advanced the plot instead?)
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Landlord: Bob route but interrupt them talking. next day advance time and look for a speech bubble at the Landlords mansion. talk to the gardener and then progress days while looking on the world map for Nagisa marker. (I'm stuck here cause I don't find the next progression step)
Can't say if it's after X days or something, but the Landlord shows up after a couple days asking for a lot of money. if you progress more days you'll have an evening with the Landlords Gardener and the scam artist in the bar. If you talk to the scam artist and reveal his intentions you avoid his route and the Landlords route will lock in
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Scam artist: Seemingly this guy starts appearing once the Landlord shows up after a couple days asking for a lot of money. if the scam artist shows up in front of the store and runs off, he'll one night show up in the bar with a speech bubble: if you talk to him and reveal he's a scam artist you avoid his route. If you ignore him or give the wrong answer you lock in his route.
True end (?): if the Landlords gardener is in the bar you can talk to him. he talks about him forgetting to feed the carps, you can go in his house, grab the bait and feed the carp. they reveal a secret about a hidden money stash you can use to blackmail the Landlord. (This night time seems to be very tight on time, cause you can mess up if you move between areas too much, because you need to also get back to the bar and shoo away the scam artist)
after you learn about the money stash you need a key from a servants room, I believe the ladder on the 2nd floor with the hole in front. I don't know how to pluck that hole yet.
If you know anything please enlighten us