If you buy used and can handle doing maintenance yourself, you can buy an older e.g. BMW convertible for less than $10k. That's somewhat cool, if you're into the whole drop top thing.
My main daily driver is a 1983 Mercedes diesel. It's likely not a car many people would consider to be "cool" but I paid less than $2000 for it, maintain it myself, enjoy doing so, and it's the most reliable car I've ever owned.
I understand that not everyone likes working on their own cars. I don't enjoy gardening. It's a diversion, a hobby for me. Like anything else, it's not "scary" once you start to understand it. It's just a machine, and in particular the older Mercedes are very overbuilt, designed to be repairable, and are generally easy to work on.
I understand that not everyone likes working on their own cars. I don't enjoy gardening. It's a diversion, a hobby for me. Like anything else, it's not "scary" once you start to understand it. It's just a machine, and in particular the older Mercedes are very overbuilt, designed to be repairable, and are generally easy to work on.