Of all my cars only one was a sad parting and that wasn't until I watched it drive off down the street for the last time. It was my
90 928 GT. I'm expecting my current 928 GTS to be a very similar experience when that day comes.
On the opposite end of the spectrum, was never so happy to see a car go as when I drove off and left the literal "pain in the butt" to drive VW Passat at the dealership when VW bought it back from me. Before they bought it back I was fantasizing abput ways to total the car and collect insurance.