I don't know if you've looked at capital gains tax rates lately but historically they are as low as they have ever been. For someone who is married and filing jointly the rate on the first $83,850 is -0-% - it can't get any lower. For the next $433,350 the tax rate is 15% and above $517,200 the rate is 20%. None of those rates are what I would call huge, although the last two are not inconsequential. My point being that you can gain $83,350 every year and never pay any tax on it . It doesn't take genius to figure out that if you spread your sales out over, let's say 5 years, you can have a total gain of $416,750 gain tax free. Remember you get to subtract pretty much every single penny you've ever put into the cars, less things like oil changes and maybe tires and batteries, from whatever you sell it for to compute your gain.