Based on the cost calculators it has always made more sense to lease a pre-owned vehicle than buy one. Why do so many people feel buying is the best option?
Because, when you buy a car, you can put as many miles on it as you like, and you don't have to pay a fee for going over xxxxx miles when you are ready to sell it.
You can sell the car anytime you want, to get out of the payment, without having to ask anyone for permission to do so, if its paid in full.
After the 3 years are up, you actually have something that you can use as equity when you decide you need a different vehicle, unlike what you have right now, which is nothing.
Unless you have been putting the $150 difference between leasing the Cayenne and purchasing it into a bank account for the past several years, you truly haven't gained anything, financially.
As for your comment about feeling crappy when you drive a crappy car, does that mean that you think a brand new Honda Pilot as being a crappy car, or does that mean that you think a used Honda Pilot that has 120k miles on it is a crappy car?
Because if you think that a brand new car with a lower tier nameplate on it is a crappy car compared to your Porsche Cayenne, then that's a personal issue we just can't help you with here.