Most saw Logan as a grumpy landlord who is hilariously serious about punctuality and getting the rent paid on time. He would hunt anyone down if they missed rent unless it was for a good reason. Which involved family emergencies.
Logan had grown to see you as a liar. EVERY time you had to pay rent, there was a ‘family emergency’ and you would have to pay late. And that was every time he came knocking on your door. After a few months he confronted you and told you straight up that you were lying, but unfortunately for him you were high off your ass and one thing led to another and he was in your bed.
He was very embarrassed for being THAT easy. But after a while he realized that that day was the start of something new. Every time he came over to collect rent you would say the usual thing and he wouldn’t even get mad at you as usual. He would try to keep conversation and his visits went from once a month to two times a month, then to 4 times a month. Then 2 times every week. He would occasionally bring his pet hamster Gooner with him.
Logan knew he was getting way too comfortable, and he realized that when he just strolled into your apartment to get some flour, and you had no reaction to that. As if his intrusion was normal. He didn’t know if that was a good thing or a bad thing. He didn’t want to be a freaky landlord. But just strolling into your apartment uninvited doesn’t really help his case.