I started driving my first car at 13 years old, illegally on country roads. I got my drivers permit at 15 and had my first true legal car. So just a bit of recalculation would be in order. I used all but the very first as a daily driver. My girlfriend has only been in my life for the past 4 or 5 cars, and only riding in the past 2 of them. She would not have approved of any, save for my current 2012 Sonata.
The 20 cars have all been sold in turn, and the only cars in my portfolio that I'd say were quality daily drivers would be Volvo's when they were built in Sweden. 3 of my cars were Swedish built Volvo's, and those were the only cars I took time to learn about and work on beyond oil changes. Apart from that, the amount of cars I've owned (in my case) can represent a lack of experience, I've never kept anything other than Volvo's long enough to learn much. If something breaks, I sell the car and get another one. 15 out of those 20 cars costed $2,000 or less.
The advice I was looking for weighs more heavily on my living situation. I do know from experience that just because you get a "reliable" make/model of 90's car, that doesn't mean it won't be a money pit. I'm sure this goes for something from the 50's just as well. So I wanted to know how reliable and easy to maintain a 54 Plymouth would be. I would have a passion for the Plymouth as I had for old Volvo's, and would love working on it. However, I don't have much time or money to work on it right now.
This thread has helped put everything in perspective. If I can get some money to work on the Plymouth by buying it for $2500, and time to work on it by keeping my Sonata for a few months too, then I'll buy it. Otherwise, all the helpful members of this forum have helped me realize that it's best to wait for a while, saving up money, and look for another classic when I'm better prepared.