tl:dr Owning a classic car was about being cheap and ended up teaching me lots.
Putting the money where your mouth is, I own a 1989 Volkswagen Cabrio. It's a silly little car that is modeled after the iconic first generation hatch backs from VW but with a convertible top. Volkswagen and convertible love aside, it's the age that matters. This year, the car will be 25 years old and will qualify for two money saving requirements of owning a car, the tags (or registration) and the insurance. Where as a standard car might set you back $140+ just to put a license on it, a classic plate will set you back about ten bucks a year. The insurance on a newer car will set you back $150 a month, if your credit is decent and you've got a good driving record (my life long accolades include neither of these). The insurance on a classic car, with full coverage, will be a fraction of that. My might Volkswagen will set me back $500 a year (with the credit of a true delinquent and the driving record to match).
Obviously, I'm a cheap skate. After selling cars for a year and a half, my greatest disbelief from the experience was how much of someone's income they were willing to give away each month, seemingly to get from point A to point B. The matter of fact is they weren't really paying for the convenience of free-will travel, I accomplished that with my cheap-o ($1000) classic car. They were paying for security.
When you've got a newer car you are buying a security blanket. The value in buying the classic car doesn't lie in it's ability to save you a bunch of money (that's just a beautiful side effect). There is something to be said about the trust you're putting in yourself that everything wont be alright. We are a society that chases convenience and comfort more than anything else and it's ruining our sense of adventure. We're not willing to do a great number of things because we wont step outside of our comfort zone and possibly get dirty.
Everyone has great potential, but it takes a great push to realize it. Often we are paralyzed by our fear of the unknown. This was described to me once as 'change only occurs when our anxiety for the current situation outweighs our anxiety for the change.' It holds true for me as it does for just about everyone else. Making the decision to do something risky get's easier and easier each time you get through the turbulence caused by the risk and you're still alive. Don't throw common sense out the window, but don't be scared either.
But what if I get stranded!?
I did, time and time again. I've seen real kindness in people as I ask random strangers for a jump, or a push. I've seen humility in asking for help from people you don't really know that well. People may surprise you, and it's endearing when someone asks you for your help.
What if I can't afford to fix it!? I'm not a mechanic!
I am, and I still can't afford to fix it. My car has been off the road since the end of Fall. I live in Michigan and there is little to no public transit anywhere. I live 120 miles from my family and am fortunate enough to have a train line between here and there. Plus, your family just might want to see you bad enough to come to you, or transport you cross state if necessary. This winter has been a testament to how tough a human can be. I've walked the majority of the time and asked for rides when it happens to line up. So far it has been a great adventure. Something I highly recommend to anyone who feels like they've been lacking something in their lives (and you probably are, trust me on this one.)