Finally have a good one to share-
A friend and coworker currently lives in a nice apartment in the downtown area that is extremely walkable/bikeable and well-serviced by public transportation, and hasn't owned a car because he lives only a few blocks away from where we work. He recently gave his notice to work for another company, where he'll be working remotely from his apartment. Nothing wrong with that decision- they offered him ~$15k more than what he's making now and it's a good company, and he's reporting to a former coworker that we both respect.
However, within a month of starting his new job he went out and bought a $40k dodge charger, which he has no need for since he works from home and really has no need for one in the area we live in! Even worse, since he didn't have a car when he moved into his apartment complex he's no longer able to purchase a full-time parking permit for the garage, so the only option was a permit that's only valid for 6pm-8am that's to be used for customer parking to the retail stores on the ground floor. This means that every day he has to wake up and go out to move his car to the street parking, and then he brings it back into the garage each night. Furthermore, there's limited long-term street parking nearby, so if it's full he has to park in the 2-hour parking zone and move it every couple hours. He's had the car for like 2 weeks and has already gotten several tickets.
He's young and is otherwise a pretty bright guy but this decision just floored me, and I made sure to tell him how stupid and impractical I think he's being!