As posted above, my parking, gas, tolls, all other incidentals are paid for on TOP of the $500/month. I currently pay 545/month for parking and I expense this without any issue. The $500 just needs to cover monthly car payment (or lease) and insurance. It is ridiculous to say I am going to have to pay out of pocket "no matter what" as I can lease a camry for 200/month + 100/month insurance and pocket 200/month Yes, i live in manhattan, and need the car for work. In what capacity i need the car is of no relevance to the original question which is.... If you had 500/month (tax free) for a car and insurance, what kind of car would you buy/lease?