Hi,
Back in 2008 I got my 4 door 65 Special from Brian Stone, and proceed to use it as a daily driver. At the time I was working in NC and going home to MI every other week (800 miles each way). Granted all the nos hoses, belts and factory style hose clamps went shortly after using the car that much, but after that it was very dependable.
I put 30,000+ miles on it over 3 years and once I finally got a job back home I used it as a daily driver for another 2 years. At that point it developed a engine issue, ring or piston and has been sidelined, but as soon as my other projects get to a point it will be back to a driver.
Currently I am fixing up a 65 Cutlass for a daily driver/cruiser. I bought all of my cars to use and enjoy.
As stated have insurance that you can live with if something does ever happen, I've been rather lucky with my old cars, unlike my 07 Ram over the last 7 months has hit 3 deer, 1 turkey and had someone run into it. So would that have happened if I was driving a old car, maybe, but either way I get to drive something I enjoy to drive, and all I can hope is something doesn't happen, only worry about what you can control, otherwise you will go nuts and having a old car will loose its appeal.
Regards,