IMHO, an old car is a hobby more than transportation, and dreams are often not for sissies.
We’ve had a “classic(?)” German car for years, and here are some considerations:
1.) They will probably be more difficult and expensive to maintain, but can be more “interesting and fun” (whatever that means) than any new car except maybe the most outrageously priced ones.
2.) On the dark side of the force … one price of buying an older car is quickly realizing how much more capable new cars are – even a cheap Chevy Cruze will easily outrun and out-handle my “classic,” although performance is rarely the charm of an older car.
3.) If you leave your common sense and buy an older "daily driver,’ consider buying one that’s in good basic shape and have a good mechanic check over the car (especially for body damage and rust!!!), because you can buy a cheap beat-up old car that will never run well or feel good. You can still wind up with a car that sucks up your money quickly (of course, even a newer Boxster or Z4 that is out of warranty can do the same) – if you buy an older car, uncertainty is something you should be philosophical about, and you need to have a bit of a gambler in you (and a sense of humor). You also just can’t flog an older car – if you don’t maintain them, garage them, wax them, keep them out of the salt/wind/rain, pamper them, avoid stressing them, etc. you can quickly turn a $50K “classic” into a $4k "junkheap."
4.) Insurance is problematic – regular insurance will not value any old car very highly, and will give you a pittance if you ever (GF) have a major accident or loss (a few body repairs can easily exceed what you would get as a settlement). You can buy a “stated value” policy from a classic car insurance specialist, but they generally have severe restrictions on your use and your annual mileage (ours won’t let us drive it to work, for example, unless it is independently garaged).
5.) Investigate car clubs for your proposed make, and examine if any shops in your local area have reliable mechanics who can work on your car – don’t buy some exotic car that no one in your locale knows how to fix properly. Many “classic” cars have available mechanical and body parts, but they ain’t cheap. Many competent mechanics enjoy working on older cars, but again, they probably won’t do it for free.
6.) Older cars need far more routine maintenance, and may require experience in things like timing and dwell, valve adjustments, carburetor settings, rust prevention, etc. We researched Corvettes, which are somehow often mentioned as simple old cars to maintain, but they are usually mentioned by people who don’t know how easily their frames can rot, how their fiberglass bodies turn to expensive spider-webbed powder, or how cheaply built they are.
7.) Many cars you mentioned (like the 190SL) are quite overpriced (like, $40K for a car that barely has 100 horsepower) – again, a good car club can help you.
8.) Finally, if safety is an issue, consider the motor scooter you mentioned may be almost as safe as some cars on your list.
Good luck.