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edit: heres the guide I found the most helpful.
https://steamcommunity.com/sharedfiles/filedetails/?id=3456491592
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But I have seen 1 exception, Crazy Frank with the pot hat will buy unlimited times per day if enough time passes. He buys 1 Gold quality coke bag from me for $ 1,500 'ish every time. I saw this when I spent lots of time building my Docks 8 mix coke automation factory.
If there is, I never reached that limit even when setting all deals to late night. It did not feel like some NPC's decided to not text me. It was all the same people as the day before, just all packed in the same time period for the deals because I chose to..
Makes sense to set them late night. Curfew bonus is nice as you said, plus nothing expires at 4 AM. You'd have to go to sleep to miss a deal.
Once their addiction level and friendliness hits high enough they will come to you randomly asking for a deal even if they already had one.