Good thread with lots of info I agree with. I've never sold a vehicle for less than I've paid in my life, (that I can remember, anyways), but I'm a cheapskate who always buys "birds with broken wings" and fixes them up. And I don't buy high mileage/rusty/ugly schitboxes no matter how cheap they are. My last DD, a Mercedes diesel, was as close to a loser as I've ever had and I sold it for exactly double what I paid 6 months ago. After factoring in parts and my labor, I probably did not break even.
My 911SC was sold for $4500 more than I paid 3 years earlier and it was also a loser after my own labor and parts were factored but it was sold under distress, (health issues), and I miss it to this day.
Whoever mentioned fuel costs gets the chicken dinner. My latest DD is a 1996 Mercedes S500 w/ low miles that I was basically given for free. (Needing a couple grand in immediate repairs/maintenance). It is a phenomenal car, quite possibly the safest car ever made and had a MSRP of ~$85k in 1996 dollars. It gets about 12mpg city on premium but ~20mpg highway. I'm almost never on the highway and L.A. freeways don't count most times because of the varying speeds. It costs me $100 a week in fuel to drive it the short distances I cover in town on a daily basis. I could lease a new Prius and fuel it for about the same $$ and have zero maintenance costs + a new car. (Or any other high-mpg economy car). It's the most expensive "free car" I've had in a while. My Mercedes diesel cost exactly half in fuel costs, even with the higher price of diesel.
FWIW, my buddy who gave me the S500 got a new BMW 335d that gets ~30mpg in town w/ no-cost maintenance for 4 years. I got repair receipts w/ the Benz showing $13k spent in the last 4 years. (He's not a car guy and was getting raped by a rip-off shop + the dealer but that's par for most owners). If he'd leased the BMW, the fuel savings alone would be over half the lease cost and it's a $57k MSRP car.
Fuel and maintenance are HUGE factors, aside from depreciation/insurance. When I look at what people spend on new luxury cars and SUVS, (total cost), it's staggering.