As stated already by one poster, it is a simple probability calculation. You have a 100% chance of saving $800 per year. The probability that you will total both of these cars in a year (or even in their remaining useful life) is too low to consider. Let's say the probability of totaling one of them in any given year is 1/60. I pick this number more or less out of the air by guessing the average driver totals one car in their 60 year driving career. If we assume the more expensive one gets it, your probable loss is 7500/60 in the first year and will decline quickly as the value of the car depreciates further. For me it is a no brainier. Drop it.