The base 718 Boxster starts at $65,000, so you’ve got room to option up. The significantly uprated GTS version I picked above starts at $92,000, so I’ve got significant problems with tax and license.
That Boxster Spider had been my first choice, so I’ll just say that I think you’ve got excellent taste. Unfortunately that starts at $102,000, and based on some very preliminary shopping for one, I’ve found they go for well over list, so you and I are both SOL in this hypothetical. And after I told my wife about the cost+markup, I’m SOL in the real world too.
The good news, should you or I pull this off, is that these retain their value. A quick search shows 2016 going for more than the new MSRP. Super limited production volumes will do that for you.
Given the restrictions of the OP I think I’d probably go for a 2023 Subaru WRX GT. New model design with plenty of bells and whistles and configurable AF so I’d probably be turning a lot of them off lol. Since I’d still have three other cars it wouldn’t be a problem if my dicky knee was acting up too much to work the clutch and since it’s not a super spendy car that I’m getting for free I won’t feel bad channelling my inner Richard Hammond to get out and flog the fuck out of it. Runs in the neighborhood of $45,000 but so much bang for the buck and actually damned practical for where I live.
2023 Lexus ES 350 ultra luxury. I am still a sedan man at heart. They start at about $51k and I figure to load it completely out.
I reckon with my average driving down to less than 12,000 miles per year (although with unlimited gas that would go up) that this car would take me to around 180k miles pretty easily. Bu then I would probably be not driving much or in some sort of self driving vehicle made for old folks.
A new Kia Soul is my choice. I almost pulled the lever on a new one in 2020 but hesitated as their DC transmissions were plagued with problems. Those have now been replaced across the line with CVT’s so my choice for the OP would the top-trim line Soul.
I’m in the team Porsche camp. A 718 Cayman GTS 4.0. I priced one online that came in at just under $100k earlier this year. Since this is a fantasy thread, part of the fantasy includes being able to get the car at MSRP in this market. Sacrifices in leather trim or the audio system could be made if needed to hit the price point.