I'm with LK on this. I always treat my rentals pretty well. Just driving around the city for work, and the rental agency does the required preventive maintenance. You then are purchasing a vehicle that's in decent condition that has already depreciated significantly, so you're purchasing just the true residual value of the vehicle. It's said that the most expensive driving "incident" you'll ever incur is when you drive the new car off the lot.
I haven't done this in the past, but I'll look into it in my next purchase.
Vehicles are not an investment. Absent a rare vehicle that becomes a classic, every vehicle will one day be sitting in a junkyard worth $0. And the time period between new purchase price and $0 is not an extremely long time, about 15 years. So unless you attribute significant value to enjoying a nice drive vs. a normal drive, it's best to buy a cheaper vehicle. I've purchased a Honda Civic for each of my kids, and I just purchased one for myself recently. Not very sexy, but I'm not either, so it suits me just fine. For $22K, it's brand spanking new, has the same interior room that an Accord had about 10 years ago, has most of the bells and whistles that I care about, and gets 40 MPG. The thing will easily give you 200-250K miles, and is dependable.
Is a nicer car more fun to drive? You bet. Is that better driving experience worth the extra $30-40K? Nope, not to me.
Not trying to be party pooper, but that's how I roll. I do have a fun car, a 1993 Dodge Viper. I take it out on sunny days,and pretend I'm cool. It's fun to drive, and with it just having under 25K miles, it's holding it's value pretty well. I'm guessing with a little TLC I could probably sell it for about $40K, which is what I paid for it about 15 years ago.