I've found that classic cars can be a challenge, as they're not "user friendly". But they reward good driving technique -- once you understand them -- far more than modern cars. Case in point: My EVO X has quicker acceleration than my 328, and has more grip in corners (AWD/torque vectoring) -- -- but all that computerized control means that it only has *one* way to get around a corner. Granted, that's the "usual" way you'd drive it alone on a track, but on the streets, there's room for more tools in the box. E.g. late braking off a high speed road onto a side street, exit speed isn't the consideration. BUT: it took me months to get used to the 328, before I was willing to push it. The EVO is fast, out of the box --- but it doesn't really get any faster with skilled technique. Okay, a couple of fair points, there. Brakes on older cares aren't up to modern standards -- mostly limited by wheel diameter. (The rotors on my EVO are larger than the *rims* on my '70s Alfa.) Side mirrors are a relatively recent innovation, where safety overrules aerodynamics. But you're looking at a "classic" as an investment -- where "originality" comes before everything. Side mirrors are easy to add, and brakes can be upgraded. But the best upgrade you can give a classic car is modern compound tires. Tire technology has come a long way. Fear of fires is model specific -- or the result of using ethanol fuel without updating fuel lines. Severe body roll is a bad suspension -- poor design or poor maintenance. Or compromise with ride comfort. Fear of break-downs is also a maintenance issue. I used Alfas as daily drivers for years --- but maintained by an excellent shop. Fear of other drivers is regional -- and is less a reflection on your vehicle than the drivers around you. (Again, this is an "investment" consideration.) But the OP premise was that neither cost nor maintenance was a consideration. A bit of a stretch, for some: I realized, a long time back, that. much as I'd like to experience a 250TR60, I'd be afraid to take a real one out of the garage -- both because of fiscal considerations, and for consideration of preserving the few that remain. And I actually got my 328 at a bit of a discount, as the previous owner didn't really understand how to drive it, so underrated it.