I have been in part time retirement mode since the end of 2019 with plans to start withdrawals in 2022. My biggest vice is probably cars... I like (and enjoy) a nice car and currently drive a 2019 AMG GT 53 and my wife drives a 2019 X5. While I don't drag around clients anymore, I "compromised" with the practical side of my brain by owning one 4 door sedan and one SUV which was good for some hardware store pickups and hauling extra peep(s) and luggage on vacations. On my car bucket list has always been a convertible 911 Cabriolet, but if I did buy this car, I feel the need to have some other vehicle with some "practicality", like a pickup, as I would not drive the 911 every day and want something else that made some sense.
So here's my rub and my questions... indulgence aside, am I setting myself up for a big disappointment (i.e. "2 best days... bought a boat/sold a boat")? For those of you who have the extra "fun" car, how often are you driving it compared to the other car? Any regrets, glad you you have the 2 car combo, do it differently next time? What cars do you own?
I get it's all personal, but curious of the experience of those who might fit in this category.