Better to do entry than buy too much. A year ago I was seriously scoping out Ford-era Aston Martin v8 Vantages
There is a lot of old money in the Chicagoland area so I saw over a half dozen and a number were going for less than 50,000 and wouldn't even be halfway to 100k miles. Did some digging on the repair bills

Just because you can buy the car doesn't mean you can afford it. If you can get a nice looking whip with some perks and YOU enjoy it, have at it.