I briefly lusted after a used Porsche Cayman. They lost about 50% in 5 years, and could be found with rather low mileage. Then I realized with minor research that the car might be cheap, but you'll be paying to maintain a $70k car, which means parts are all 2-3x, labor at the Porsche dealer would be 3-5x, etc. The sexy mental image quickly soured and i can't see used Porsches, BMW's, and Mercedes as anything beyond giant money pits.
Maybe someday after retirement I will pickup turning wrenches as a hobby, but for now just maintaining my bicycle has been an obnoxious time sink I have taken to outsourcing now and then.