For whatever it's worth, some random thoughts, different perspective:
If you have had a lifelong passion for cars but are finding that missing now, maybe try some good journalism. Call it changing your diet. There is stuff like
https://www.sfchronicle.com/local/ar...g-16137119.php , a guy who imported a Japanese micro fire truck. Or
https://jalopnik.com/project-vemac-h...e-j-1846862024 about a guy restoring an obscure racer. Possibly someone else's passion will infuse yours.
Maybe a partner in crime with different character. Maybe you are missing the adventure in owning a car, things you might find in the seat of an older classic. You have to make a lot of compromises along with older cars, for sure, but that can be part of the joy. The car I miss for example is a 911E sunroof coupe. Those early 911's are just so much fun to drive. The car just spoke to me in a way. Whatever Corvette, S2000, Audi, M I have tried, they are all just much, much faster but they have never spoken to me the same way. Maybe is there some classic ride for you?
Maybe your passion is calling for something unique. With the money you are talking, you could certainly look at replicas for example. You could build a classic exactly the way you want it start-to-finish, forever yours.
I find my passion refreshed by weekends at the track. I don't need to be racing to enjoy it. Something I love about the weekend ET drag series out here is that there are so many cool cars. People build and race so many cool cars. The events are cheap to attend and the people are fellow travelers.