I own a townhouse with a double-wide driveway. The 2 spots in front of my garage are mine. You’d be surprised how many people don’t get it. When the neighbors friends are waiting for him to come out, I don’t bother unless I happen to be leaving anyway. But I have also told a delivery truck that they either need to move their vehicle in the next 5 minutes, or pay the $60 fee for me missing my appointment. My other neighbor has had it worse, she has woken up half the neighborhood banging on the door of her shared driveway because they blocked her in overnight. Several times.
Are these different people every time, or one guy dropping off his wife weekly? I would walk out and ask if he’s lost or needing assistance, if he asks at that point you can reply that he can stay for now but in the future this is a private driveway.